Reaction of β-Nitrostyrene with Diethyl Malonate in the Presence of Bispidines: The Unusual Role of the Organocatalyst
The aim of this work was the investigation of novel organocatalysts for the Michael addition of diethyl malonate to β-nitrostyrene. The methodology of the study included NMR titration, reaction monitoring by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), product characteriz...
Saved in:
| Published in | Chemistry an international journal Vol. 6; no. 3; pp. 387 - 406 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Basel
MDPI AG
01.06.2024
|
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | The aim of this work was the investigation of novel organocatalysts for the Michael addition of diethyl malonate to β-nitrostyrene. The methodology of the study included NMR titration, reaction monitoring by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), product characterization by MALDI, IR spectroscopy, scanning electron microscopy (SEM), thermal gravimetric analysis (TGA), and elemental analysis. As a result, evidence of supramolecular interactions between two pairs of components of the reaction was found. In addition to the supramolecular complexes, an unusual reaction, i.e., the Michael addition of NH-bispidines to β-nitrostyrene, was found, which led to previously unknown oligomers of β-nitrostyrene. A new mechanism for the catalytic action of NH-bispidine was proposed, which involved catalysis not by the initial organocatalyst but rather by its adduct with β-nitrostyrene. Thus, in this reaction, N-benzylbispidine acted as an initiator, and the real catalyst was the betaine formed during the initiation stage. |
|---|---|
| AbstractList | The aim of this work was the investigation of novel organocatalysts for the Michael addition of diethyl malonate to β-nitrostyrene. The methodology of the study included NMR titration, reaction monitoring by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), product characterization by MALDI, IR spectroscopy, scanning electron microscopy (SEM), thermal gravimetric analysis (TGA), and elemental analysis. As a result, evidence of supramolecular interactions between two pairs of components of the reaction was found. In addition to the supramolecular complexes, an unusual reaction, i.e., the Michael addition of NH-bispidines to β-nitrostyrene, was found, which led to previously unknown oligomers of β-nitrostyrene. A new mechanism for the catalytic action of NH-bispidine was proposed, which involved catalysis not by the initial organocatalyst but rather by its adduct with β-nitrostyrene. Thus, in this reaction, N-benzylbispidine acted as an initiator, and the real catalyst was the betaine formed during the initiation stage. |
| Author | Mamedova, Sabina F. Vatsadze, Sergey Z. Dalinger, Alexander I. Burykina, Julia V. Pentsak, Evgeniy O. |
| Author_xml | – sequence: 1 givenname: Alexander I. orcidid: 0000-0002-6568-3186 surname: Dalinger fullname: Dalinger, Alexander I. – sequence: 2 givenname: Sabina F. surname: Mamedova fullname: Mamedova, Sabina F. – sequence: 3 givenname: Julia V. orcidid: 0000-0001-6286-1699 surname: Burykina fullname: Burykina, Julia V. – sequence: 4 givenname: Evgeniy O. orcidid: 0000-0001-9040-0013 surname: Pentsak fullname: Pentsak, Evgeniy O. – sequence: 5 givenname: Sergey Z. orcidid: 0000-0001-7884-8579 surname: Vatsadze fullname: Vatsadze, Sergey Z. |
| BookMark | eNp1UUtr3DAQFiWBpknuOQp6divrZau3Nn0F0iaE5CxmpXFWiyNtJS3Bf6s_pL-pdraUEuhphpnvMcz3ihzEFJGQs5a9EcKwt26ND6HUPGkmGOPiBTnimsumV9Ic_NO_JKelbNgMUUwapY_I4w2CqyFFmgb662fzPdScSp0yRqSPoa7px4B1PY30G4wpQkUaIq1rpNcZC0aHC_FDKNvgQ8Tyjt7Ou7u4KzsY6U0an_YL_irfQ0wOKoxTqSfkcICx4OmfekzuPn-6Pf_aXF59uTh_f9k4qXhtnJDKoBvalgP3ndCgBwErUFIOTLPeKO6871vWKqdBAPoVg16i6xU6Y7Q4Jhd7XZ9gY7c5PECebIJgnwYp31vINbgRrfHoB-06gG4lFRrgnUc5qFlw8KYTs9brvdY2px87LNVu0i7H-XwrWMe5kVwtjmyPcvMjS8bhr2vL7JKWfZ7WTNHPKC5UWFKpGcL4f-Jvs2KhGA |
| CitedBy_id | crossref_primary_10_1007_s11164_024_05382_7 |
| Cites_doi | 10.1021/acs.orglett.0c03305 10.1002/chem.200700097 10.1002/anie.200704280 10.1002/chem.202104524 10.1016/j.tetasy.2008.05.006 10.1002/ejoc.201900956 10.1007/s10517-016-3198-4 10.1016/j.tet.2011.08.070 10.1039/C8NJ01930D 10.1002/cjoc.201800155 10.1021/ja060338e 10.1016/j.chempr.2019.02.027 10.1134/S1070428020110123 10.1016/j.tet.2004.06.141 10.1039/D2SC00446A 10.1007/s11172-014-0526-6 10.1002/adsc.202000875 10.1111/j.1527-3458.2001.tb00206.x 10.1002/macp.1984.021850314 10.1111/j.1527-3458.2001.tb00211.x 10.1007/s10787-020-00705-7 10.1515/zna-1978-0301 10.1021/jo0343026 10.1039/c3ob41122b 10.1002/1521-3765(20021018)8:20<4767::AID-CHEM4767>3.0.CO;2-O 10.1021/acsmedchemlett.1c00299 10.1134/S1070428013050047 10.1070/RC2013v082n07ABEH004413 10.1021/acs.chemrev.7b00692 10.3390/molecules26247539 10.1021/ja800839w 10.3390/nano9010089 10.1021/ja052935r 10.1080/00222337708063081 10.1080/00397911.2011.580880 10.1002/anie.200800847 10.1002/(SICI)1099-0690(200002)2000:3<391::AID-EJOC391>3.0.CO;2-R 10.1002/anie.199014221 10.1021/acs.joc.2c01339 10.1021/ja0735913 10.2174/157017806777828529 10.1002/adsc.200800341 10.1016/j.tetasy.2007.02.024 10.1002/pol.1978.170160507 10.1021/acs.joc.6b00218 10.1021/ja01233a509 10.1021/ja01279a004 10.1002/adsc.201100636 10.1021/jo0604991 10.1007/s11172-011-0399-x 10.1002/anie.200801130 10.1021/ol060398p 10.1055/s-0035-1560420 10.1002/adsc.200505199 10.1002/chin.201007024 10.1002/chem.201605033 10.1016/0032-3861(73)90113-4 10.1002/1521-3765(20010202)7:3<671::AID-CHEM671>3.0.CO;2-M 10.3390/catal11091134 10.1002/chem.201604110 10.1021/ja044370p 10.1002/chem.201502090 10.1021/ja046296g 10.1002/asia.200600093 10.1002/anie.200463058 10.1021/ja058772o 10.1021/acschemneuro.0c00254 10.1016/j.ejmech.2020.112726 10.1016/j.tet.2014.10.042 10.1016/j.tetlet.2005.05.139 10.1002/poc.2909 10.1021/ja01405a031 |
| ContentType | Journal Article |
| Copyright | 2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. |
| Copyright_xml | – notice: 2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. |
| DBID | AAYXX CITATION 8FE 8FG ABJCF ABUWG AFKRA AZQEC BENPR BGLVJ CCPQU COVID D1I DWQXO HCIFZ KB. PDBOC PHGZM PHGZT PIMPY PKEHL PQEST PQGLB PQQKQ PQUKI PRINS DOA |
| DOI | 10.3390/chemistry6030023 |
| DatabaseName | CrossRef ProQuest SciTech Collection ProQuest Technology Collection Materials Science & Engineering Collection ProQuest Central (Alumni) ProQuest Central UK/Ireland ProQuest Central Essentials ProQuest Central Technology Collection ProQuest One Coronavirus Research Database ProQuest Materials Science Collection ProQuest Central Korea SciTech Premium Collection Materials Science Database Materials Science Collection ProQuest Central Premium ProQuest One Academic (New) Publicly Available Content Database ProQuest One Academic Middle East (New) ProQuest One Academic Eastern Edition (DO NOT USE) ProQuest One Applied & Life Sciences ProQuest One Academic ProQuest One Academic UKI Edition ProQuest Central China DOAJ Open Access Journals |
| DatabaseTitle | CrossRef Publicly Available Content Database ProQuest Materials Science Collection Technology Collection ProQuest One Academic Middle East (New) ProQuest Central Essentials ProQuest One Academic Eastern Edition Materials Science Collection Coronavirus Research Database ProQuest Central (Alumni Edition) SciTech Premium Collection ProQuest One Community College ProQuest Technology Collection ProQuest SciTech Collection ProQuest Central China ProQuest Central ProQuest One Applied & Life Sciences ProQuest One Academic UKI Edition ProQuest Central Korea Materials Science & Engineering Collection Materials Science Database ProQuest Central (New) ProQuest One Academic ProQuest One Academic (New) |
| DatabaseTitleList | Publicly Available Content Database CrossRef |
| Database_xml | – sequence: 1 dbid: DOA name: DOAJ Directory of Open Access Journals url: https://www.doaj.org/ sourceTypes: Open Website – sequence: 2 dbid: 8FG name: ProQuest Technology Collection url: https://search.proquest.com/technologycollection1 sourceTypes: Aggregation Database |
| DeliveryMethod | fulltext_linktorsrc |
| EISSN | 2624-8549 |
| EndPage | 406 |
| ExternalDocumentID | oai_doaj_org_article_9dedf6c7aa7b45e9a27de4f50a8fd973 10_3390_chemistry6030023 |
| GeographicLocations | United States--US Germany |
| GeographicLocations_xml | – name: United States--US – name: Germany |
| GroupedDBID | AADQD AAFWJ AAYXX ABDBF ABJCF AFKRA AFPKN AFZYC ALMA_UNASSIGNED_HOLDINGS BENPR BGLVJ CCPQU CITATION GROUPED_DOAJ HCIFZ IAO IGS ISR ITC KB. MODMG OK1 PDBOC PHGZM PHGZT PIMPY 8FE 8FG ABUWG AZQEC COVID D1I DWQXO PKEHL PQEST PQGLB PQQKQ PQUKI PRINS PUEGO |
| ID | FETCH-LOGICAL-c452t-c3459ecf112a2d736a6f3aba544f0608952cdd81015c6a3aedb0a84ec85ec9963 |
| IEDL.DBID | BENPR |
| ISSN | 2624-8549 |
| IngestDate | Wed Aug 27 01:32:19 EDT 2025 Fri Jul 25 11:48:35 EDT 2025 Tue Jul 01 01:21:06 EDT 2025 Thu Apr 24 22:59:39 EDT 2025 |
| IsDoiOpenAccess | true |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 3 |
| Language | English |
| License | https://creativecommons.org/licenses/by/4.0 |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c452t-c3459ecf112a2d736a6f3aba544f0608952cdd81015c6a3aedb0a84ec85ec9963 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 |
| ORCID | 0000-0001-7884-8579 0000-0001-6286-1699 0000-0001-9040-0013 0000-0002-6568-3186 |
| OpenAccessLink | https://www.proquest.com/docview/3072294256?pq-origsite=%requestingapplication% |
| PQID | 3072294256 |
| PQPubID | 5046913 |
| PageCount | 20 |
| ParticipantIDs | doaj_primary_oai_doaj_org_article_9dedf6c7aa7b45e9a27de4f50a8fd973 proquest_journals_3072294256 crossref_primary_10_3390_chemistry6030023 crossref_citationtrail_10_3390_chemistry6030023 |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2024-06-01 |
| PublicationDateYYYYMMDD | 2024-06-01 |
| PublicationDate_xml | – month: 06 year: 2024 text: 2024-06-01 day: 01 |
| PublicationDecade | 2020 |
| PublicationPlace | Basel |
| PublicationPlace_xml | – name: Basel |
| PublicationTitle | Chemistry an international journal |
| PublicationYear | 2024 |
| Publisher | MDPI AG |
| Publisher_xml | – name: MDPI AG |
| References | Watanabe (ref_26) 2004; 126 Okino (ref_32) 2005; 127 Schnabel (ref_66) 1977; 11 Hoppe (ref_46) 1990; 29 Huttenloch (ref_44) 2001; 7 Janka (ref_25) 2006; 128 Nori (ref_8) 2022; 28 Gandelman (ref_21) 2005; 44 ref_53 Huttenloch (ref_43) 2002; 8 Kent (ref_11) 2020; 11 Kachala (ref_74) 2013; 82 Scharnagel (ref_37) 2015; 21 Worrall (ref_58) 1944; 66 Cui (ref_72) 2012; 25 Liu (ref_51) 2008; 130 Zheng (ref_3) 2018; 118 Li (ref_34) 2011; 67 Lesma (ref_47) 2007; 18 Sokolova (ref_55) 2020; 207 Tsakos (ref_7) 2012; 354 Toom (ref_67) 2006; 71 Li (ref_50) 2022; 13 Ogawa (ref_19) 2006; 1 Zhang (ref_40) 2011; 396–398 Kaljurand (ref_68) 2007; 13 Zhu (ref_16) 2006; 7 Rossetti (ref_38) 2018; 42 Mase (ref_64) 2006; 128 Worrall (ref_60) 1927; 49 Silvani (ref_39) 2006; 3 Liu (ref_48) 2018; 36 ref_71 Nichols (ref_24) 2006; 8 Anderson (ref_56) 2014; 70 Shcherbakov (ref_57) 2022; 13 Reznikov (ref_23) 2013; 49 Tshepelevitsh (ref_69) 2019; 2019 Halder (ref_29) 2008; 47 Kashin (ref_75) 2011; 60 Buendia (ref_6) 2020; 362 ref_73 Tyurenkov (ref_13) 2016; 160 Evans (ref_22) 2005; 127 Jin (ref_31) 2016; 81 Silverman (ref_14) 2008; 47 Mozhaitsev (ref_36) 2020; 56 Spieler (ref_41) 2000; 2000 Halland (ref_20) 2003; 68 Marchetti (ref_33) 2019; 5 Berry (ref_61) 1973; 14 Bilka (ref_35) 2016; 48 Zvejniece (ref_15) 2020; 28 Evans (ref_5) 2007; 129 Hamashima (ref_18) 2005; 347 Worrall (ref_59) 1938; 60 Berry (ref_62) 1984; 185 Hayashi (ref_30) 2008; 47 Schnabel (ref_65) 1978; 33 Li (ref_49) 2020; 22 ref_42 Vatsadze (ref_70) 2014; 63 ref_1 Hui (ref_10) 2017; 23 Afanasyev (ref_4) 2022; 87 ref_2 Ohshima (ref_28) 2004; 60 ref_9 Majima (ref_27) 2005; 46 Wen (ref_17) 2012; 42 Carter (ref_63) 1978; 16 Lapin (ref_12) 2006; 7 Yang (ref_52) 2008; 350 Lesma (ref_45) 2008; 19 Roy (ref_54) 2017; 23 |
| References_xml | – volume: 22 start-page: 8708 year: 2020 ident: ref_49 article-title: A Bispidine-Based Chiral Amine Catalyst for Asymmetric Mannich Reaction of Ketones with Isatin Ketimines publication-title: Org. Lett. doi: 10.1021/acs.orglett.0c03305 – volume: 13 start-page: 7631 year: 2007 ident: ref_68 article-title: Brønsted Basicities of Diamines in the Gas Phase, Acetonitrile, and Tetrahydrofuran publication-title: Chem. Eur. J. doi: 10.1002/chem.200700097 – volume: 47 start-page: 3500 year: 2008 ident: ref_14 article-title: From Basic Science to Blockbuster Drug: The Discovery of Lyrica publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200704280 – volume: 28 start-page: e202104524 year: 2022 ident: ref_8 article-title: DoE-Driven Development of an Organocatalytic Enantioselective Addition of Acetaldehyde to Nitrostyrenes in Water publication-title: Chem. A Eur. J. doi: 10.1002/chem.202104524 – volume: 19 start-page: 1363 year: 2008 ident: ref_45 article-title: New chiral diamino ligands as sparteine analogues. Application to the palladium-catalyzed kinetic oxidative resolution of 1-phenyl ethanol publication-title: Tetrahedron Asymmetry doi: 10.1016/j.tetasy.2008.05.006 – volume: 2019 start-page: 6735 year: 2019 ident: ref_69 article-title: On the Basicity of Organic Bases in Different Media publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.201900956 – volume: 160 start-page: 465 year: 2016 ident: ref_13 article-title: Comparison of Nootropic and Neuroprotective Features of Aryl-Substituted Analogs of Gamma-Aminobutyric Acid publication-title: Bull. Exp. Biol. Med. doi: 10.1007/s10517-016-3198-4 – volume: 67 start-page: 10186 year: 2011 ident: ref_34 article-title: Biscinchona alkaloids as highly efficient bifunctional organocatalysts for the asymmetric conjugate addition of malonates to nitroalkenes at ambient temperature publication-title: Tetrahedron doi: 10.1016/j.tet.2011.08.070 – volume: 42 start-page: 12072 year: 2018 ident: ref_38 article-title: Application of chiral bi- and tetra-dentate bispidine-derived ligands in the copper(II)-catalyzed asymmetric Henry reaction publication-title: New J. Chem. doi: 10.1039/C8NJ01930D – volume: 36 start-page: 791 year: 2018 ident: ref_48 article-title: Chiral Amino Acids-Derived Catalysts and Ligands publication-title: Chin. J. Chem. doi: 10.1002/cjoc.201800155 – volume: 128 start-page: 4966 year: 2006 ident: ref_64 article-title: Organocatalytic Direct Michael Reaction of Ketones and Aldehydes with β-Nitrostyrene in Brine publication-title: J. Am. Chem. Soc. doi: 10.1021/ja060338e – ident: ref_1 – volume: 5 start-page: 1398 year: 2019 ident: ref_33 article-title: The Versatility of Squaramides: From Supramolecular Chemistry to Chemical Biology publication-title: Chem doi: 10.1016/j.chempr.2019.02.027 – volume: 56 start-page: 1969 year: 2020 ident: ref_36 article-title: Conjugates of Bispidine and Monoterpenoids as Ligands of Metal Complex Catalysts for the Henry Reaction publication-title: Russ. J. Org. Chem. doi: 10.1134/S1070428020110123 – volume: 396–398 start-page: 1236 year: 2011 ident: ref_40 article-title: Synthesis of Chiral Tridentate Ligands Embodying the Bispidine Framework and their Application in the Enantioselective Addition of Diethylzinc to Aldehydes publication-title: Adv. Mater. Res. – volume: 60 start-page: 9569 year: 2004 ident: ref_28 article-title: Enantioselective total synthesis of (−)-strychnine: Development of a highly practical catalytic asymmetric carbon–carbon bond formation and domino cyclization publication-title: Tetrahedron doi: 10.1016/j.tet.2004.06.141 – volume: 13 start-page: 4313 year: 2022 ident: ref_50 article-title: Water enables diastereodivergency in bispidine-based chiral amine-catalyzed asymmetric Mannich reaction of cyclic N-sulfonyl ketimines with ketones publication-title: Chem. Sci. doi: 10.1039/D2SC00446A – volume: 63 start-page: 895 year: 2014 ident: ref_70 article-title: New supramolecular synthons based on 3d transition metal complexes with bidentate bispidines: Synthesis and structural, spectroscopic, and electrochemical studies publication-title: Russ. Chem. Bull. doi: 10.1007/s11172-014-0526-6 – volume: 362 start-page: 5506 year: 2020 ident: ref_6 article-title: A Nickel-Bisdiamine Porous Organic Polymer as Heterogeneous Chiral Catalyst for Asymmetric Michael Addition to Aliphatic Nitroalkenes publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.202000875 – volume: 7 start-page: 387 year: 2006 ident: ref_16 article-title: The Antidepressant and Antiinflammatory Effects of Rolipram in the Central Nervous System publication-title: CNS Drug Rev. doi: 10.1111/j.1527-3458.2001.tb00206.x – volume: 185 start-page: 559 year: 1984 ident: ref_62 article-title: Anionic polymerization of β-nitrostyrenes publication-title: Makromol. Chem. doi: 10.1002/macp.1984.021850314 – volume: 7 start-page: 471 year: 2006 ident: ref_12 article-title: Phenibut (β-Phenyl-GABA): A Tranquilizer and Nootropic Drug publication-title: CNS Drug Rev. doi: 10.1111/j.1527-3458.2001.tb00211.x – volume: 28 start-page: 1283 year: 2020 ident: ref_15 article-title: Neuroprotective and anti-inflammatory activity of DAT inhibitor R-phenylpiracetam in experimental models of inflammation in male mice publication-title: Inflammopharmacology doi: 10.1007/s10787-020-00705-7 – volume: 33 start-page: 253 year: 1978 ident: ref_65 article-title: Primary Reactions during the Free Anionic Polymerization of β Nitrostyrene publication-title: Z. Naturforsch. A doi: 10.1515/zna-1978-0301 – volume: 68 start-page: 5067 year: 2003 ident: ref_20 article-title: Direct Asymmetric Michael Reactions of Cyclic 1,3-Dicarbonyl Compounds and Enamines Catalyzed by Chiral Bisoxazoline−Copper(II) Complexes publication-title: J. Org. Chem. doi: 10.1021/jo0343026 – ident: ref_73 doi: 10.1039/c3ob41122b – volume: 8 start-page: 4767 year: 2002 ident: ref_43 article-title: Solid-phase development of chiral phosphoramidite ligands for enantioselective conjugate addition reactions publication-title: Chem. Eur. J. doi: 10.1002/1521-3765(20021018)8:20<4767::AID-CHEM4767>3.0.CO;2-O – volume: 13 start-page: 140 year: 2022 ident: ref_57 article-title: Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors publication-title: ACS Med. Chem. Lett. doi: 10.1021/acsmedchemlett.1c00299 – volume: 49 start-page: 663 year: 2013 ident: ref_23 article-title: Enantioselective synthesis of γ-aminobutyric acid derivatives by Ni(II)-catalyzed reaction of diethyl malonate with nitroalkenes publication-title: Russ. J. Org. Chem. doi: 10.1134/S1070428013050047 – volume: 82 start-page: 648 year: 2013 ident: ref_74 article-title: Target-oriented analysis of gaseous, liquid and solid chemical systems by mass spectrometry, nuclear magnetic resonance spectroscopy and electron microscopy publication-title: Russ. Chem. Rev. doi: 10.1070/RC2013v082n07ABEH004413 – volume: 118 start-page: 7586 year: 2018 ident: ref_3 article-title: Recent Advances in Metal-Catalyzed Asymmetric 1,4-Conjugate Addition (ACA) of Nonorganometallic Nucleophiles publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.7b00692 – ident: ref_42 doi: 10.3390/molecules26247539 – volume: 130 start-page: 5654 year: 2008 ident: ref_51 article-title: Asymmetric Direct Aldol Reaction of Functionalized Ketones Catalyzed by Amine Organocatalysts Based on Bispidine publication-title: J. Am. Chem. Soc. doi: 10.1021/ja800839w – ident: ref_71 doi: 10.3390/nano9010089 – volume: 127 start-page: 9958 year: 2005 ident: ref_22 article-title: Ni(II)−Bis[(R,R)-N,N′-dibenzylcyclohexane-1,2-diamine]Br2 Catalyzed Enantioselective Michael Additions of 1,3-Dicarbonyl Compounds to Conjugated Nitroalkenes publication-title: J. Am. Chem. Soc. doi: 10.1021/ja052935r – volume: 11 start-page: 1637 year: 1977 ident: ref_66 article-title: Anionic Polymerization of β-Nitrostyrene under the Influence of High Energy Radiation publication-title: J. Macromol. Sci. Part A Chem. doi: 10.1080/00222337708063081 – volume: 42 start-page: 3288 year: 2012 ident: ref_17 article-title: Practical Large-Scale Preparation of (R)-Rolipram Using Chiral Nickel Catalyst publication-title: Synth. Commun. doi: 10.1080/00397911.2011.580880 – volume: 47 start-page: 4719 year: 2008 ident: ref_29 article-title: Catalytic Asymmetric Michael Reactions of Acetaldehyde publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200800847 – volume: 2000 start-page: 391 year: 2000 ident: ref_41 article-title: Synthesis of chiral amino alcohols embodying the bispidine framework and their application as ligands in enantioselectively catalyzed additions to C=O and C=C groups publication-title: Eur. J. Org. Chem. doi: 10.1002/(SICI)1099-0690(200002)2000:3<391::AID-EJOC391>3.0.CO;2-R – volume: 29 start-page: 1422 year: 1990 ident: ref_46 article-title: Chiral Lithium-1-oxyalkanides by Asymmetric Deprotonation; Enantioselective Synthesis of 2-Hydroxyalkanoic Acids and Secondary Alkanols publication-title: Angew. Chem. Int. Ed. Engl. doi: 10.1002/anie.199014221 – volume: 87 start-page: 12182 year: 2022 ident: ref_4 article-title: Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins publication-title: J. Org. Chem. doi: 10.1021/acs.joc.2c01339 – volume: 129 start-page: 11583 year: 2007 ident: ref_5 article-title: Scope and Mechanism of Enantioselective Michael Additions of 1,3-Dicarbonyl Compounds to Nitroalkenes Catalyzed by Nickel(II)−Diamine Complexes publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0735913 – volume: 3 start-page: 430 year: 2006 ident: ref_39 article-title: Chiral Amino-Amides as Solution Phase and Immobilized Ligands for the Catalytic Asymmetric Alkylation of Aromatic Aldehydes publication-title: Lett. Org. Chem. doi: 10.2174/157017806777828529 – volume: 350 start-page: 2001 year: 2008 ident: ref_52 article-title: Highly Efficient Amine Organocatalysts Based on Bispidine for the Asymmetric Michael Addition of Ketones to Nitroolefins publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.200800341 – volume: 18 start-page: 659 year: 2007 ident: ref_47 article-title: Enantioselective copper-catalyzed cyclopropanation of styrene by means of chiral bispidine ligands publication-title: Tetrahedron Asymmetry doi: 10.1016/j.tetasy.2007.02.024 – volume: 16 start-page: 937 year: 1978 ident: ref_63 article-title: Anionic-initiated polymerization of β-nitrostyrenes publication-title: J. Polym. Sci. Polym. Chem. Ed. doi: 10.1002/pol.1978.170160507 – volume: 81 start-page: 3263 year: 2016 ident: ref_31 article-title: L-Proline Derived Bifunctional Organocatalysts: Enantioselective Michael Addition of Dithiomalonates to trans-β-Nitroolefins publication-title: J. Org. Chem. doi: 10.1021/acs.joc.6b00218 – volume: 66 start-page: 842 year: 1944 ident: ref_58 article-title: p-Dimethylamino Derivatives of Nitrostyrene publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01233a509 – volume: 60 start-page: 2841 year: 1938 ident: ref_59 article-title: The Action of Ammonia and Aromatic Amines on 4-Methylnitrostyrene and Related Compounds publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01279a004 – volume: 354 start-page: 740 year: 2012 ident: ref_7 article-title: Primary Amine-Thioureas with Improved Catalytic Properties for “Difficult” Michael Reactions: Efficient Organocatalytic Syntheses of (S)-Baclofen, (R)-Baclofen and (S)-Phenibut publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.201100636 – volume: 71 start-page: 7155 year: 2006 ident: ref_67 article-title: Substituent Effects on the Basicity of 3,7-Diazabicyclo[3.3.1]nonanes publication-title: J. Org. Chem. doi: 10.1021/jo0604991 – volume: 60 start-page: 2602 year: 2011 ident: ref_75 article-title: A SEM study of nanosized metal films and metal nanoparticles obtained by magnetron sputtering publication-title: Russ. Chem. Bull. doi: 10.1007/s11172-011-0399-x – volume: 47 start-page: 4722 year: 2008 ident: ref_30 article-title: Asymmetric Michael Reaction of Acetaldehyde Catalyzed by Diphenylprolinol Silyl Ether publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200801130 – volume: 8 start-page: 1495 year: 2006 ident: ref_24 article-title: Preparation of Pyrrolidine-Based PDE4 Inhibitors via Enantioselective Conjugate Addition of α-Substituted Malonates to Aromatic Nitroalkenes publication-title: Org. Lett. doi: 10.1021/ol060398p – volume: 48 start-page: 1474 year: 2016 ident: ref_35 article-title: Squaramide-Catalyzed Michael Addition as a Key Step for the Direct Synthesis of GABAergic Drugs publication-title: Synthesis doi: 10.1055/s-0035-1560420 – volume: 347 start-page: 1576 year: 2005 ident: ref_18 article-title: Catalytic Enantioselective Michael Reaction of 1,3-Dicarbonyl Compoundsvia Formation of Chiral Palladium Enolate publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.200505199 – ident: ref_53 doi: 10.1002/chin.201007024 – volume: 23 start-page: 1241 year: 2017 ident: ref_54 article-title: pH-Gated Chloride Transport by a Triazine-Based Tripodal Semicage publication-title: Chem. Eur. J. doi: 10.1002/chem.201605033 – volume: 14 start-page: 172 year: 1973 ident: ref_61 article-title: Anionic polymerization of β-nitrostyrene publication-title: Polymer doi: 10.1016/0032-3861(73)90113-4 – volume: 7 start-page: 671 year: 2001 ident: ref_44 article-title: Chiral Bicyclic Phosphoramidites—A New Class of Ligands for Asymmetric Catalysis publication-title: Chem. Eur. J. doi: 10.1002/1521-3765(20010202)7:3<671::AID-CHEM671>3.0.CO;2-M – ident: ref_9 doi: 10.3390/catal11091134 – volume: 23 start-page: 4023 year: 2017 ident: ref_10 article-title: Metal-Catalyzed Asymmetric Michael Addition in Natural Product Synthesis publication-title: Chem. A Eur. J. doi: 10.1002/chem.201604110 – volume: 127 start-page: 119 year: 2005 ident: ref_32 article-title: Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea publication-title: J. Am. Chem. Soc. doi: 10.1021/ja044370p – volume: 21 start-page: 12488 year: 2015 ident: ref_37 article-title: The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions publication-title: Chem. A Eur. J. doi: 10.1002/chem.201502090 – ident: ref_2 – volume: 126 start-page: 11148 year: 2004 ident: ref_26 article-title: Catalytic Enantioselective Michael Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes Catalyzed by Well-Defined Chiral Ru Amido Complexes publication-title: J. Am. Chem. Soc. doi: 10.1021/ja046296g – volume: 1 start-page: 121 year: 2006 ident: ref_19 article-title: Chiral Scandium Catalysts for Enantioselective Michael Reactions of β-Ketoesters publication-title: Chem. Asian J. doi: 10.1002/asia.200600093 – volume: 44 start-page: 2393 year: 2005 ident: ref_21 article-title: Highly Enantioselective Catalytic Conjugate Addition of N-Heterocycles to α,β-Unsaturated Ketones and Imides publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200463058 – volume: 128 start-page: 5312 year: 2006 ident: ref_25 article-title: Tandem Nazarov Cyclization−Michael Addition Sequence Catalyzed by an Ir(III) Complex publication-title: J. Am. Chem. Soc. doi: 10.1021/ja058772o – volume: 11 start-page: 1740 year: 2020 ident: ref_11 article-title: Classics in Chemical Neuroscience: Baclofen publication-title: ACS Chem. Neurosci. doi: 10.1021/acschemneuro.0c00254 – volume: 207 start-page: 112726 year: 2020 ident: ref_55 article-title: Monoterpenoid-based inhibitors of filoviruses targeting the glycoprotein-mediated entry process publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2020.112726 – volume: 70 start-page: 9337 year: 2014 ident: ref_56 article-title: Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes publication-title: Tetrahedron doi: 10.1016/j.tet.2014.10.042 – volume: 46 start-page: 5377 year: 2005 ident: ref_27 article-title: Enantio- and diastereoselective construction of vicinal quaternary and tertiary carbon centers by catalytic Michael reaction of α-substituted β-keto esters to cyclic enones publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2005.05.139 – volume: 25 start-page: 814 year: 2012 ident: ref_72 article-title: Degradation of dichloromethane by bispidine publication-title: J. Phys. Org. Chem. doi: 10.1002/poc.2909 – volume: 49 start-page: 1598 year: 1927 ident: ref_60 article-title: The Addition of Amino and Hydrazino Bases to Nitrostyrene 1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01405a031 |
| SSID | ssj0002504956 |
| Score | 2.278775 |
| Snippet | The aim of this work was the investigation of novel organocatalysts for the Michael addition of diethyl malonate to β-nitrostyrene. The methodology of the... |
| SourceID | doaj proquest crossref |
| SourceType | Open Website Aggregation Database Enrichment Source Index Database |
| StartPage | 387 |
| SubjectTerms | Aluminum bispidines Calibration Catalysis Chemical analysis Chromatography Infrared spectroscopy Mass spectrometry Michael addition monoterpenoids Nitrogen nitroolefins NMR spectroscopy Software Thermal analysis Thermogravimetric analysis Titration β-nitrostyrene |
| SummonAdditionalLinks | – databaseName: DOAJ Open Access Journals dbid: DOA link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV3NTtwwELYqTlyqIqhYSpEPXDhEmzr-iXuDFoSQQBViJW6RM55IkVZZ1M0K8Vp9kD4TM04WUZDohWtix9F4PP5m7PlGiEMsdTTgXIbRxIzwrcq8U5hFZ2oofalrz8nJl1f2fKYvbs3ts1JffCdsoAceBDf1EWNjwYXgam3QB-Ui6sbkoWyid4nnk_a8Z84U22Am5iLkP5xLFuTXT2FdP82SWueq-GcfSnT9r6xx2mLOPomPIzaUx8M_bYkP2G2L-2sccg_kopF__2RXbc-JGg9MRSk5iip_tkjSnsvLMOdQOMq2kwTr5K-UWQTIHU_a5V0b-Yr7d0maIWfdarmisa4X8_Se26e0zEWK5zws-x0xOzu9-XGejdUSMtBG9RkU2niEhgBUUNEVNtimCHUwWje5zUtvFMTIfF4GbCgCxppkqBFKg0BeT_FZbHSLDneFVLZWCoJGAjs6B1Py8Rl5kkDf-AYNTMR0LbsKRipxrmgxr8ilYGlXL6U9EUdPPe4GGo032p7wdDy1YwLs9IDUohrVovqfWkzE_noyq3FVLiuyZ0p5slJ27z3G-CI2FUGc4eLYvtjof6_wK0GUvj5I2vgIpkjqRA priority: 102 providerName: Directory of Open Access Journals |
| Title | Reaction of β-Nitrostyrene with Diethyl Malonate in the Presence of Bispidines: The Unusual Role of the Organocatalyst |
| URI | https://www.proquest.com/docview/3072294256 https://doaj.org/article/9dedf6c7aa7b45e9a27de4f50a8fd973 |
| Volume | 6 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV3NbtQwELZoe-GCQIAolJUPXDhYGxz_cqlY2qVC6qpasVJvkTN2UKRVsm2yQn2tPgjPxNjJbgVIvcY_UcbjyXxjzzeEfAhGeAlas-ClZ-jfcmY1D8xrWYKxRpQ2JidfLtTFSny_ltdjwK0br1XubGIy1L6FGCOfoi5yblHD1OnmhsWqUfF0dSyhcUCO0AQbBF9Hs_PF1XIfZYkEXYgAhvPJHPH9FHZ11BSqd8bzv_5Hibb_P6ucfjXz5-TZ6CPSL8OiviBPQvOS_FqGIQeBthX9fc8WdR8TNu4iJSWN0VR6VgeU-ppeunUMiQdaNxTdO3qVMowgxIGzutvUPl51_0xRQ-iq2XZbfNeyXaf22D-lZ7YprnPX9a_Ian7-4-sFG6smMBCS9wxyIW2ACh0px73OlVNV7konhagylRkrOXgfeb0kKJe74MvMGRHAyACIfvLX5LBpm_CGUK5KzsGJgE6PyECaeIyGiBJwjk9QwTGZ7mRXwEgpHitbrAuEFlHaxb_SPiYf9yM2A53GI31ncTn2_SIRdnrQ3v4sxn1VWB98pUA7p0shg3Vc-yAqiZ9UeatxkpPdYhbj7uyKB116-3jzO_KUoxMzXA07IYf97Ta8RyekLyfkwMy_TUZ9myQo_wcYeeNA |
| linkProvider | ProQuest |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtV3NbtQwELZKOcAFgQBRKOADHDhEGxw7iZEQopRlS7srVHWl3oIznqBIq2TpZlXtS3HgQXgmZvKzCJB66zV2HGXms_3N2DMjxAtMtTeQJAF64wPityqwicLAJyaH1KY6txycPJ3Fk7n-fG7Od8SPIRaGr1UOa2K7UPsa2Ec-IiwqZQlh8bvl94CrRvHp6lBCo4PFMW4uyWRbvT06JP2-VGr88ezDJOirCgSgjWoCiLSxCAURDad8EsUuLiKXO6N1EcZhao0C7znvlYHYRQ59HrpUI6QGgayDiMa9IW7qKLI8o9Lxp61Ph9OBkb3RnYZSeziCoWpbTJMpVNFfu19bJOC_PaDd2MZ3xZ2ekcr3HYTuiR2s7ovLU-wiHmRdyF8_g1nZcHjIhhNgSvbdysMSSccLOXULdsCjLCtJZFJ-aeOZAPnFg3K1LD1frH8jCY9yXq1Xa_rWab1o27l_Gwxat16kzap5IObXIs2HYreqK3wkpIpzpcBpJIqlQzApH9qR_Qo0xmsoYE-MBtll0Ccw5zoai4wMGZZ29q-098Sr7RvLLnnHFX0PWB3bfpx2u31QX3zL-lmcWY--iCFxLsm1QetU4lEXhn6p8DahQfYHZWb9WrDK_iD38dXNz8Wtydn0JDs5mh0_EbcV0afuUtq-2G0u1viU6E-TP2sxJ8XX6wb5b5CmHWQ |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtV1Lb9QwELbKVkJcEAgQhQI-wIFDtMGx47gSQizbVUvparVipd6CM3ZQpFWybXZV7d_iyI_gNzGTxyJA6q3X-KXMfLZnxvNg7LVPpFOgdeCdcgHKtyIwWvjAaZVBYhKZGQpOPp_GJwv5-UJd7LGffSwMuVX2Z2JzULsKyEY-RCwKYRBh8TDv3CJm48mH1WVAFaTopbUvp9FC5Mxvr1F9q9-fjpHXb4SYHH_9dBJ0FQYCkEqsA4ikMh5yFDqscDqKbZxHNrNKyjyMw8QoAc5RDiwFsY2sd1loE-khUR5QU4hw3jtsX6NWFA7Y_uh4OpvvLDyUHAy1j_ZtNIpMOIS-hluMWysU0V93YVMy4L8bobnmJg_Y_U4-5R9bQD1ke758xK7nvo1_4FXOf_0IpsWagkW2lA6TkyWXjwuPHF_yc7skc7znRclRtOSzJroJPA0cFfWqcORmf8QRnXxRbuoNrjWvlk079W9CQ6vGprSt14_Z4lbo-YQNyqr0TxkXcSYEWOlR4JIhqISe8FCbBZzjHeRwwIY97VLo0plTVY1limoNUTv9l9oH7O1uxKpN5XFD3xGxY9ePknA3H6qr72m3p1PjvMtj0NbqTCpvrNDOy1zhL-XOaJzksGdm2p0MdfoHx89ubn7F7iLA0y-n07Pn7J5AWar1UDtkg_XVxr9AWWidvexAx9m328b5bybqIvY |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Reaction+of+%CE%B2-Nitrostyrene+with+Diethyl+Malonate+in+the+Presence+of+Bispidines%3A+The+Unusual+Role+of+the+Organocatalyst&rft.jtitle=Chemistry+an+international+journal&rft.au=Dalinger%2C+Alexander+I&rft.au=Mamedova%2C+Sabina+F&rft.au=Burykina%2C+Julia+V&rft.au=Pentsak%2C+Evgeniy+O&rft.date=2024-06-01&rft.pub=MDPI+AG&rft.eissn=2624-8549&rft.volume=6&rft.issue=3&rft.spage=387&rft_id=info:doi/10.3390%2Fchemistry6030023&rft.externalDBID=HAS_PDF_LINK |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=2624-8549&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=2624-8549&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=2624-8549&client=summon |