Copper- and Silver-Catalyzed Diastereo- and Enantioselective Conjugate Addition Reaction of 1‑Pyrroline Esters to Nitroalkenes: Diastereoselectivity Switch by Chiral Metal Complexes
syn-Diastereoselective conjugate addition of 1-pyrroline esters to nitroalkenes in good yields with an excellent enantioselectivity by using CuOAc/Me-FcPHOX catalyst in the presence of pyridine. In contrast, AgOAc/tBu-ThioClickFerrophos catalyzed the anti diastereoselective conjugate addition with a...
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| Published in | Journal of organic chemistry Vol. 80; no. 21; pp. 10883 - 10891 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
06.11.2015
Amer Chemical Soc |
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| Abstract | syn-Diastereoselective conjugate addition of 1-pyrroline esters to nitroalkenes in good yields with an excellent enantioselectivity by using CuOAc/Me-FcPHOX catalyst in the presence of pyridine. In contrast, AgOAc/tBu-ThioClickFerrophos catalyzed the anti diastereoselective conjugate addition with a high enantioselectivity without additional base. Thus, the preparation of chiral 1-pyrroline derivatives bearing diverse stereochemistry could be achieved. The diastereoselective reduction of the imine group in the conjugate adduct could afford the 2,5-cis-proline ester derivative. |
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| AbstractList | syn-Diastereoselective conjugate addition of 1-pyrroline esters to nitroalkenes in good yields with an excellent enantioselectivity by using CuOAc/Me-FcPHOX catalyst in the presence of pyridine. In contrast, AgOAc/tBu-ThioClickFerrophos catalyzed the anti diastereoselective conjugate addition with a high enantioselectivity without additional base. Thus, the preparation of chiral 1-pyrroline derivatives bearing diverse stereochemistry could be achieved. The diastereoselective reduction of the imine group in the conjugate adduct could afford the 2,5-cis-proline ester derivative. |
| Author | Arai, Yuri Koizumi, Akihiro Tokoro, Yuichiro Fukuzawa, Shin-ichi Kimura, Midori |
| AuthorAffiliation | Department of Applied Chemistry, Institute of Science and Engineering Chuo University |
| AuthorAffiliation_xml | – name: Department of Applied Chemistry, Institute of Science and Engineering – name: Chuo University |
| Author_xml | – sequence: 1 givenname: Akihiro surname: Koizumi fullname: Koizumi, Akihiro – sequence: 2 givenname: Midori surname: Kimura fullname: Kimura, Midori – sequence: 3 givenname: Yuri surname: Arai fullname: Arai, Yuri – sequence: 4 givenname: Yuichiro surname: Tokoro fullname: Tokoro, Yuichiro – sequence: 5 givenname: Shin-ichi surname: Fukuzawa fullname: Fukuzawa, Shin-ichi email: orgsynth@kc.chuo-u.ac.jp |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26426827$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1002/jcc.20495 10.1021/ja2100356 10.1021/om300435s 10.1021/ja100265j 10.1039/b913066g 10.1002/chem.201100374 10.1021/ol4006618 10.1016/j.bmcl.2008.11.004 10.1021/ol301916t 10.1021/ol100060t 10.1055/s-0034-1378649 10.1016/j.tetlet.2014.09.070 10.1021/ar2000343 10.1021/ol0520370 10.1002/chem.201103876 10.1021/cn900037c 10.1002/anie.201206835 10.1002/wcms.81 10.1016/j.tetlet.2013.01.130 10.1039/c4cc04381b 10.1002/anie.201307392 10.1039/c4cc01692k 10.1039/c3ob27089k 10.1021/ja0552186 10.1016/j.tetasy.2013.05.023 10.1039/c1cc10779h 10.1002/ejoc.200700267 10.1002/anie.201204394 10.1016/j.tetlet.2010.07.085 10.1002/anie.200805063 10.1021/ja500878c 10.1002/anie.200503672 10.1021/acs.orglett.5b00277 10.1016/j.tet.2007.03.130 10.1002/jcc.21759 10.1021/ol4019584 10.1246/cl.130504 10.1021/ol0516925 10.1021/ol100336q 10.1016/j.tetlet.2013.12.101 10.1021/jo2003727 10.1039/c2cc17149j 10.1063/1.3382344 10.1021/ol060314c 10.1039/c3cc43824d 10.1021/ol300431n 10.1039/c5ob00591d 10.1002/chem.200903443 10.1002/anie.201501100 10.1016/j.tetasy.2015.02.009 10.1002/adsc.201400563 10.1063/1.463096 10.1039/b508541a 10.1039/C4CC04381B 10.1039/C5OB00591D 10.1271/bbb.69.867 |
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| Keywords | ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION DESIGN PYRROLIDINES LIGANDS GLYCINE IMINO ESTER CONSTRUCTION AZOMETHINE YLIDES BASIS-SETS DERIVATIVES MICHAEL ADDITION |
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| References | Hernandez-Toribio, J (WOS:000292095800009) 2011; 17 Kim, HY (WOS:000298571600024) 2011; 133 Llamas, T (WOS:000237174500012) 2006; 8 Grimme, S (WOS:000276971500005) 2010; 132 Teng, HL (WOS:000332922600054) 2014; 136 Wang, MY (WOS:000311466300020) 2012; 31 Najera, C (WOS:000250545100008) 2007; 2007 Adrio, J (WOS:000342992000003) 2014; 50 Shin-ya, K (WOS:000229575000001) 2005; 69 Dai, L (WOS:000353085000005) 2015; 26 Takahashi, K (WOS:000301516000072) 2012; 14 Imae, K (WOS:000289956900078) 2011; 76 Narayan, R (WOS:000327410300020) 2013; 52 Yan, XX (WOS:000236119000037) 2006; 45 Bai, XF (WOS:000354190800053) 2015; 54 Arai, T (WOS:000276797800007) 2010; 132 Yu, J (WOS:000297483100003) 2011; 44 Ayan, S (WOS:000322610500011) 2013; 24 Gonzalez-Esguevillas, M (WOS:000299503600028) 2012; 48 Zhang, W (WOS:000322805500001) 2013; 42 Garner, P (WOS:000334736900010) 2014; 50 Robles-Machin, R (WOS:000277988900005) 2010; 16 Li, Q (WOS:000274841800047) 2010; 12 Watanabe, S (WOS:000331509800009) 2014; 55 SCHAFER, A (WOS:A1992JJ41100041) 1992; 97 Potowski, M (WOS:000322915200012) 2013; 49 Castello, LM (WOS:000346071600019) 2014; 356 Vaswani, RG (WOS:000261908600028) 2009; 19 Potowski, M (WOS:000308713300005) 2012; 51 Neese, F (WOS:000298355300004) 2012; 2 Tada, A (WOS:000344204600017) 2014; 55 Konno, T (WOS:000328864800037) 2013; 15 Liu, TL (WOS:000305388300011) 2012; 18 Cabrera, S (WOS:000252081800024) 2007; 63 Shirakawa, S (WOS:000317615000003) 2013; 52 Najera, C (WOS:000271432300001) 2009; 7 Zeng, W (WOS:000232817700068) 2005; 7 Imae, K (WOS:000308390000029) 2012; 14 Xue, ZY (WOS:000354205600021) 2015; 13 Li, JY (WOS:000350841300058) 2015; 17 Grimme, S (WOS:000288871100026) 2011; 32 Gao, WZ (WOS:000231858100045) 2005; 7 Xue, ZY (WOS:000345328700009) 2014; 25 Lopez-Perez, A (WOS:000262458300016) 2009; 48 Lee, M (WOS:000315464900016) 2013; 11 Weigend, F (WOS:000231618300007) 2005; 7 Castello, LM (WOS:000320979000004) 2013; 15 Oura, I (WOS:000276562600027) 2010; 12 Adrio, J (WOS:000291395800003) 2011; 47 Limon, A (WOS:000277981000003) 2010; 1 Grimme, S (WOS:000241477200003) 2006; 27 Chandan, N (WOS:000316534500020) 2013; 54 Shimizu, K (WOS:000281626100039) 2010; 51 Cabrera, S (WOS:000233617900027) 2005; 127 ref9/cit9 ref1/cit1e ref1/cit1d ref2/cit2g ref2/cit2f ref2/cit2e ref2/cit2d ref13/cit13a ref13/cit13b ref13/cit13c ref13/cit13d ref13/cit13e ref12/cit12c ref13/cit13f ref12/cit12b ref12/cit12a ref2/cit2c ref8/cit8 ref2/cit2b ref2/cit2a ref1/cit1a ref1/cit1c ref1/cit1b ref11/cit11f ref3/cit3b ref11/cit11c ref3/cit3c ref11/cit11b ref11/cit11e ref3/cit3a ref11/cit11d ref11/cit11a ref6/cit6 ref15/cit15a ref10/cit10d ref15/cit15d ref10/cit10e ref15/cit15e ref10/cit10f ref15/cit15b ref10/cit10g ref15/cit15c ref10/cit10a ref10/cit10b ref15/cit15f ref10/cit10c ref5/cit5 ref4/cit4a ref4/cit4b ref4/cit4c ref4/cit4d ref4/cit4e ref4/cit4f ref7/cit7 |
| References_xml | – volume: 27 start-page: 1787 year: 2006 ident: WOS:000241477200003 article-title: Semiempirical GGA-type density functional constructed with a long-range dispersion correction publication-title: JOURNAL OF COMPUTATIONAL CHEMISTRY doi: 10.1002/jcc.20495 contributor: fullname: Grimme, S – volume: 133 start-page: 20750 year: 2011 ident: WOS:000298571600024 article-title: Stereodivergency in Catalytic Asymmetric Conjugate Addition Reactions of Glycine (Ket)imines publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja2100356 contributor: fullname: Kim, HY – volume: 31 start-page: 7870 year: 2012 ident: WOS:000311466300020 article-title: Cu(I)/TF-BiphamPhos Catalyzed Reactions of Alkylidene Bisphosphates and Alkylidene Malonates with Azomethine Ylides: Michael Addition versus 1,3-Dipolar Cycloaddition publication-title: ORGANOMETALLICS doi: 10.1021/om300435s contributor: fullname: Wang, MY – volume: 132 start-page: 5338 year: 2010 ident: WOS:000276797800007 article-title: Chiral Bis(imidazolidine)pyridine-Cu(OTf)(2): Catalytic Asymmetric Endo-Selective [3+2] Cycloaddition of Imino Esters with Nitroalkenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja100265j contributor: fullname: Arai, T – volume: 7 start-page: 4567 year: 2009 ident: WOS:000271432300001 article-title: 1,3-Dipolar cycloadditions: applications to the synthesis of antiviral agents publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/b913066g contributor: fullname: Najera, C – volume: 17 start-page: 6334 year: 2011 ident: WOS:000292095800009 article-title: Enantiocontrolled Synthesis of beta-Branched alpha-Amino Acids by Using Cu-I-Catalyzed 1,4-Addition of Glycine Imines to beta-Substituted gem-Diactivated Olefins publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201100374 contributor: fullname: Hernandez-Toribio, J – volume: 15 start-page: 2902 year: 2013 ident: WOS:000320979000004 article-title: Phosphoramidite-Cu(OTf)(2) Complexes as Chiral Catalysts for 1,3-Dipolar Cycloaddition of lminoesters and Nitroalkenes publication-title: ORGANIC LETTERS doi: 10.1021/ol4006618 contributor: fullname: Castello, LM – volume: 19 start-page: 132 year: 2009 ident: WOS:000261908600028 article-title: Design, synthesis, and biological evaluation of a scaffold for iGluR ligands based on the structure of (-)-kaitocephalin publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS doi: 10.1016/j.bmcl.2008.11.004 contributor: fullname: Vaswani, RG – volume: 14 start-page: 4410 year: 2012 ident: WOS:000308390000029 article-title: Silver/ThioClickFerrophos-Catalyzed Enantioselective Conjugate Addition and Cycloaddition of Glycine Imino Ester with Nitroalkenes publication-title: ORGANIC LETTERS doi: 10.1021/ol301916t contributor: fullname: Imae, K – volume: 12 start-page: 1080 year: 2010 ident: WOS:000274841800047 article-title: Diastereo- and Enantioselective Synthesis of alpha,gamma-Diaminobutyric Acid Derivatives via Cu-Catalyzed Asymmetric Michael Reaction publication-title: ORGANIC LETTERS doi: 10.1021/ol100060t contributor: fullname: Li, Q – volume: 25 start-page: 2733 year: 2014 ident: WOS:000345328700009 article-title: Catalytic Asymmetric Construction of Azabicyclo[2.2.1] heptanes Bearing Two Quaternary Stereogenic Centers via Silver(I)-Catalyzed 1,3-Dipolar Cycloaddition of Cyclic Azomethine Ylides publication-title: SYNLETT doi: 10.1055/s-0034-1378649 contributor: fullname: Xue, ZY – volume: 55 start-page: 6224 year: 2014 ident: WOS:000344204600017 article-title: Synthesis of 7-azabicyclo[2.2.1]heptane-1-carboxylate via silver/ThioClickFerrophos-catalyzed asymmetric 1,3-dipolar cycloaddition of dihydropyrrole ester with N-substituted maleimide publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2014.09.070 contributor: fullname: Tada, A – volume: 44 start-page: 1156 year: 2011 ident: WOS:000297483100003 article-title: Bronsted-Acid-Catalyzed Asymmetric Multicomponent Reactions for the Facile Synthesis of Highly Enantioenriched Structurally Diverse Nitrogenous Heterocycles publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar2000343 contributor: fullname: Yu, J – volume: 7 start-page: 5055 year: 2005 ident: WOS:000232817700068 article-title: Bifunctional AgOAc-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides publication-title: ORGANIC LETTERS doi: 10.1021/ol0520370 contributor: fullname: Zeng, W – volume: 18 start-page: 8042 year: 2012 ident: WOS:000305388300011 article-title: Stereoselective Construction of Spiro(butyrolactonepyrrolidines) by Highly Efficient Copper(I)/TF-BiphamPhos-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201103876 contributor: fullname: Liu, TL – volume: 1 start-page: 175 year: 2010 ident: WOS:000277981000003 article-title: Kaitocephalin Antagonism of Glutamate Receptors Expressed in Xenopus Oocytes publication-title: ACS CHEMICAL NEUROSCIENCE doi: 10.1021/cn900037c contributor: fullname: Limon, A – volume: 52 start-page: 4312 year: 2013 ident: WOS:000317615000003 article-title: Recent Developments in Asymmetric Phase-Transfer Reactions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201206835 contributor: fullname: Shirakawa, S – volume: 2 start-page: 73 year: 2012 ident: WOS:000298355300004 article-title: The ORCA program system publication-title: WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL MOLECULAR SCIENCE doi: 10.1002/wcms.81 contributor: fullname: Neese, F – volume: 54 start-page: 1987 year: 2013 ident: WOS:000316534500020 article-title: A direct route to 2,2,5-trisubstituted pyrrolidines of relevance to kaitocephalin publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2013.01.130 contributor: fullname: Chandan, N – volume: 50 start-page: 12434 year: 2014 ident: WOS:000342992000003 article-title: Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c4cc04381b contributor: fullname: Adrio, J – volume: 52 start-page: 12892 year: 2013 ident: WOS:000327410300020 article-title: Catalytic Enantioselective Synthesis of Functionalized Tropanes Reveals Novel Inhibitors of Hedgehog Signaling publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201307392 contributor: fullname: Narayan, R – volume: 50 start-page: 4908 year: 2014 ident: WOS:000334736900010 article-title: A concise [C plus NC plus CC] coupling-enabled synthesis of kaitocephalin publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c4cc01692k contributor: fullname: Garner, P – volume: 11 start-page: 2039 year: 2013 ident: WOS:000315464900016 article-title: Highly enantioselective synthesis of 5-phenyl-2-alkylprolines using phase-transfer catalytic alkylation publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c3ob27089k contributor: fullname: Lee, M – volume: 127 start-page: 16394 year: 2005 ident: WOS:000233617900027 article-title: Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0552186 contributor: fullname: Cabrera, S – volume: 24 start-page: 838 year: 2013 ident: WOS:000322610500011 article-title: Asymmetric synthesis and molecular docking study of enantiomerically pure pyrrolidine derivatives with potential antithrombin activity publication-title: TETRAHEDRON-ASYMMETRY doi: 10.1016/j.tetasy.2013.05.023 contributor: fullname: Ayan, S – volume: 47 start-page: 6784 year: 2011 ident: WOS:000291395800003 article-title: Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c1cc10779h contributor: fullname: Adrio, J – volume: 2007 start-page: 5038 year: 2007 ident: WOS:000250545100008 article-title: Diastereoselective 1,3-dipolar cycloaddition reactions between azomethine ylides and chiral acrylates derived from methyl (S)- and (R)-Lactate synthesis of hepatitis C virus RNA-Dependent RNA polymerase inhibitors publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.200700267 contributor: fullname: Najera, C – volume: 7 start-page: 3297 year: 2005 ident: WOS:000231618300007 article-title: Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy publication-title: PHYSICAL CHEMISTRY CHEMICAL PHYSICS contributor: fullname: Weigend, F – volume: 51 start-page: 9512 year: 2012 ident: WOS:000308713300005 article-title: Highly Enantioselective Catalytic [6+3] Cycloadditions of Azomethine Ylides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201204394 contributor: fullname: Potowski, M – volume: 51 start-page: 5068 year: 2010 ident: WOS:000281626100039 article-title: Ag/ThioClickFerrophos catalyzed highly enantioselective 1,3-dipolar cycloaddition of azomethine ylides with alkenes publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2010.07.085 contributor: fullname: Shimizu, K – volume: 48 start-page: 340 year: 2009 ident: WOS:000262458300016 article-title: The Phenylsulfonyl Group as a Temporal Regiochemical Controller in the Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200805063 contributor: fullname: Lopez-Perez, A – volume: 136 start-page: 4075 year: 2014 ident: WOS:000332922600054 article-title: Cu(I)-Catalyzed Regio- and Stereoselective [6+3] Cycloaddition of Azomethine Ylides with Tropone: An Efficient Asymmetric Access to Bridged Azabicyclo[4.3.1]decadienes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja500878c contributor: fullname: Teng, HL – volume: 45 start-page: 1979 year: 2006 ident: WOS:000236119000037 article-title: A highly enantio- and diastereoselective Cu-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with nitroalkenes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200503672 contributor: fullname: Yan, XX – volume: 17 start-page: 1288 year: 2015 ident: WOS:000350841300058 article-title: Brucine Diol-Copper-Catalyzed Asymmetric Synthesis of endo-Pyrrolidines: The Mechanistic Dichotomy of Imino Esters publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b00277 contributor: fullname: Li, JY – volume: 63 start-page: 6587 year: 2007 ident: WOS:000252081800024 article-title: Cu-I-fesulphos complexes: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides publication-title: TETRAHEDRON doi: 10.1016/j.tet.2007.03.130 contributor: fullname: Cabrera, S – volume: 32 start-page: 1456 year: 2011 ident: WOS:000288871100026 article-title: Effect of the Damping Function in Dispersion Corrected Density Functional Theory publication-title: JOURNAL OF COMPUTATIONAL CHEMISTRY doi: 10.1002/jcc.21759 contributor: fullname: Grimme, S – volume: 69 start-page: 867 year: 2005 ident: WOS:000229575000001 article-title: Novel antitumor and neuroprotective substances discovered by characteristic screenings based on specific molecular targets publication-title: BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY contributor: fullname: Shin-ya, K – volume: 15 start-page: 4418 year: 2013 ident: WOS:000328864800037 article-title: Silver/ThioClickFerrophos Complex as an Effective Catalyst for Asymmetric Conjugate Addition of Glycine Imino Ester to Unsaturated Malonates and alpha-Enones publication-title: ORGANIC LETTERS doi: 10.1021/ol4019584 contributor: fullname: Konno, T – volume: 42 start-page: 676 year: 2013 ident: WOS:000322805500001 article-title: 1,3-Dipolar Cycloaddition-based Synthesis of Diverse Heterocyclic Scaffolds publication-title: CHEMISTRY LETTERS doi: 10.1246/cl.130504 contributor: fullname: Zhang, W – volume: 7 start-page: 4241 year: 2005 ident: WOS:000231858100045 article-title: Cu(I)-catalyzed highly exo-selective and enantioselective [3+2] cycloaddition of azomethine ylides with acrylates publication-title: ORGANIC LETTERS doi: 10.1021/ol0516925 contributor: fullname: Gao, WZ – volume: 12 start-page: 1752 year: 2010 ident: WOS:000276562600027 article-title: Highly Endo-Selective and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylide with alpha-Enones Catalyzed by a Silver(I)/ThioClickFerrophos Complex publication-title: ORGANIC LETTERS doi: 10.1021/ol100336q contributor: fullname: Oura, I – volume: 55 start-page: 1306 year: 2014 ident: WOS:000331509800009 article-title: Bifunctional AgOAc/ThioClickFerrophos complex-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with aryl- and alkylidene malonates publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2013.12.101 contributor: fullname: Watanabe, S – volume: 76 start-page: 3604 year: 2011 ident: WOS:000289956900078 article-title: Ag/ThioClickFerrophos-Catalyzed Enantioselective Mannich Reaction and Amination of Glycine Schiff Base publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo2003727 contributor: fullname: Imae, K – volume: 97 start-page: 2571 year: 1992 ident: WOS:A1992JJ41100041 article-title: FULLY OPTIMIZED CONTRACTED GAUSSIAN-BASIS SETS FOR ATOMS LI TO KR publication-title: JOURNAL OF CHEMICAL PHYSICS contributor: fullname: SCHAFER, A – volume: 48 start-page: 2149 year: 2012 ident: WOS:000299503600028 article-title: Cu-catalyzed asymmetric [3+2] cycloaddition of alpha-iminoamides with activated olefins publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c2cc17149j contributor: fullname: Gonzalez-Esguevillas, M – volume: 132 start-page: ARTN 154104 year: 2010 ident: WOS:000276971500005 article-title: A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu publication-title: JOURNAL OF CHEMICAL PHYSICS doi: 10.1063/1.3382344 contributor: fullname: Grimme, S – volume: 8 start-page: 1795 year: 2006 ident: WOS:000237174500012 article-title: Catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones publication-title: ORGANIC LETTERS doi: 10.1021/ol060314c contributor: fullname: Llamas, T – volume: 49 start-page: 7800 year: 2013 ident: WOS:000322915200012 article-title: Catalytic asymmetric exo-selective [6+3] cycloaddition of iminoesters with fulvenes publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c3cc43824d contributor: fullname: Potowski, M – volume: 14 start-page: 1644 year: 2012 ident: WOS:000301516000072 article-title: Total Synthesis of (-)-Kaitocephalin Based on a Rh-Catalyzed C-H Amination publication-title: ORGANIC LETTERS doi: 10.1021/ol300431n contributor: fullname: Takahashi, K – volume: 13 start-page: 5460 year: 2015 ident: WOS:000354205600021 article-title: Cu(I)/TF-BiphamPhos-catalyzed asymmetric Michael addition of cyclic ketimino esters to alkylidene malonates publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c5ob00591d contributor: fullname: Xue, ZY – volume: 16 start-page: 5286 year: 2010 ident: WOS:000277988900005 article-title: Catalytic Asymmetric 1,3-Dipolar Cycloaddition of alpha-Iminonitriles publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200903443 contributor: fullname: Robles-Machin, R – volume: 54 start-page: 5255 year: 2015 ident: WOS:000354190800053 article-title: Aromatic Amide-Derived Non-Biaryl Atropisomers as Highly Efficient Ligands in Silver-Catalyzed Asymmetric Cycloaddition Reactions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201501100 contributor: fullname: Bai, XF – volume: 26 start-page: 350 year: 2015 ident: WOS:000353085000005 article-title: The design, synthesis and application of imidazolium-tagged ferrocenyl oxazoline phosphine ligands for the asymmetric 1,3-dipolar cycloaddition of azomethine ylides with nitroalkenes: ion effect for enhancing the reactivity, stereoselectivity and recyclability publication-title: TETRAHEDRON-ASYMMETRY doi: 10.1016/j.tetasy.2015.02.009 contributor: fullname: Dai, L – volume: 356 start-page: 3861 year: 2014 ident: WOS:000346071600019 article-title: Efficient Diastereo- and Enantioselective Synthesis of exo-Nitroprolinates by 1,3-Dipolar Cycloadditions Catalyzed by Chiral Phosphoramidite.Silver(I) Complexes publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201400563 contributor: fullname: Castello, LM – ident: ref1/cit1b doi: 10.1246/cl.130504 – ident: ref12/cit12c doi: 10.1021/ol0520370 – ident: ref2/cit2b doi: 10.1002/anie.201501100 – ident: ref10/cit10a doi: 10.1016/j.tetasy.2015.02.009 – ident: ref6/cit6 doi: 10.1002/anie.201307392 – ident: ref15/cit15c doi: 10.1002/jcc.21759 – ident: ref13/cit13f doi: 10.1021/ja0552186 – ident: ref3/cit3c doi: 10.1002/ejoc.200700267 – ident: ref2/cit2c doi: 10.1021/ja500878c – ident: ref2/cit2f doi: 10.1002/chem.201103876 – ident: ref4/cit4b doi: 10.1021/ol4019584 – ident: ref1/cit1c doi: 10.1002/anie.201206835 – ident: ref15/cit15e doi: 10.1063/1.463096 – ident: ref15/cit15d doi: 10.1063/1.3382344 – ident: ref10/cit10g doi: 10.1002/anie.200503672 – ident: ref12/cit12b doi: 10.1021/ol0516925 – ident: ref13/cit13d doi: 10.1016/j.tet.2007.03.130 – ident: ref8/cit8 doi: 10.1055/s-0034-1378649 – ident: ref2/cit2a doi: 10.1021/acs.orglett.5b00277 – ident: ref4/cit4d doi: 10.1021/jo2003727 – ident: ref10/cit10f doi: 10.1002/adsc.201400563 – ident: ref15/cit15a doi: 10.1002/wcms.81 – ident: ref15/cit15f doi: 10.1039/b508541a – ident: ref13/cit13a doi: 10.1002/chem.201100374 – ident: ref12/cit12a doi: 10.1021/ol100060t – ident: ref13/cit13b doi: 10.1002/chem.200903443 – ident: ref11/cit11d doi: 10.1021/cn900037c – ident: ref13/cit13e doi: 10.1021/ol060314c – ident: ref10/cit10e doi: 10.1021/ja100265j – ident: ref3/cit3a doi: 10.1016/j.tetasy.2013.05.023 – ident: ref1/cit1d doi: 10.1039/c1cc10779h – ident: ref7/cit7 doi: 10.1016/j.tetlet.2014.09.070 – ident: ref11/cit11b doi: 10.1016/j.tetlet.2013.01.130 – ident: ref1/cit1a doi: 10.1039/C4CC04381B – ident: ref11/cit11e doi: 10.1016/j.bmcl.2008.11.004 – ident: ref3/cit3b doi: 10.1039/b913066g – ident: ref11/cit11c doi: 10.1021/ol300431n – ident: ref15/cit15b doi: 10.1002/jcc.20495 – ident: ref10/cit10c doi: 10.1039/c2cc17149j – ident: ref11/cit11a doi: 10.1039/c4cc01692k – ident: ref2/cit2d doi: 10.1039/c3cc43824d – ident: ref4/cit4c doi: 10.1021/ol301916t – ident: ref9/cit9 doi: 10.1039/C5OB00591D – ident: ref10/cit10d doi: 10.1021/ja2100356 – ident: ref4/cit4e doi: 10.1021/ol100336q – ident: ref2/cit2e doi: 10.1002/anie.201204394 – ident: ref4/cit4f doi: 10.1016/j.tetlet.2010.07.085 – ident: ref10/cit10b doi: 10.1021/ol4006618 – ident: ref5/cit5 doi: 10.1039/c3ob27089k – ident: ref2/cit2g doi: 10.1021/om300435s – ident: ref1/cit1e doi: 10.1021/ar2000343 – ident: ref13/cit13c doi: 10.1002/anie.200805063 – ident: ref4/cit4a doi: 10.1016/j.tetlet.2013.12.101 – ident: ref11/cit11f doi: 10.1271/bbb.69.867 |
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| Snippet | syn-Diastereoselective conjugate addition of 1-pyrroline esters to nitroalkenes in good yields with an excellent enantioselectivity by using CuOAc/Me-FcPHOX... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Copper- and Silver-Catalyzed Diastereo- and Enantioselective Conjugate Addition Reaction of 1‑Pyrroline Esters to Nitroalkenes: Diastereoselectivity Switch by Chiral Metal Complexes |
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