Manganese(I)-Catalyzed Asymmetric Hydrophosphination of α,β‑Unsaturated Carbonyl Derivatives
Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H–P bond activation, various phosphine-containing chiral products can be accessed via hydrophosphination of various ketone-, ester-, and carboxamide-bas...
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Published in | Organic letters Vol. 25; no. 10; pp. 1611 - 1615 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
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American Chemical Society
17.03.2023
Amer Chemical Soc |
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Abstract | Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H–P bond activation, various phosphine-containing chiral products can be accessed via hydrophosphination of various ketone-, ester-, and carboxamide-based Michael acceptors. |
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AbstractList | Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H–P bond activation, various phosphine-containing chiral products can be accessed via hydrophosphination of various ketone-, ester-, and carboxamide-based Michael acceptors. Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H-P bond activation, various phosphine-containing chiral products can be accessed via hydrophosphination of various ketone-, ester-, and carboxamide-based Michael acceptors. Here we report catalytic asymmetric hydrophosphi-nation of a,P-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H-P bond activation, various phosphine-containing chiral products can be accessed via hydro-phosphination of various ketone-, ester-, and carboxamide-based Michael acceptors. Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H–P bond activation, various phosphine-containing chiral products can be accessed via hydrophosphination of various ketone-, ester-, and carboxamide-based Michael acceptors. |
Author | Harutyunyan, Syuzanna R. Sinnema, Esther G. Castiñeira Reis, Marta Ge, Luo Postolache, Roxana Pérez, Juana M. |
AuthorAffiliation | Stratingh Institute for Chemistry |
AuthorAffiliation_xml | – name: Stratingh Institute for Chemistry |
Author_xml | – sequence: 1 givenname: Roxana surname: Postolache fullname: Postolache, Roxana – sequence: 2 givenname: Juana M. orcidid: 0000-0002-6495-2591 surname: Pérez fullname: Pérez, Juana M. – sequence: 3 givenname: Marta orcidid: 0000-0003-4204-3474 surname: Castiñeira Reis fullname: Castiñeira Reis, Marta – sequence: 4 givenname: Luo orcidid: 0000-0001-9964-5156 surname: Ge fullname: Ge, Luo – sequence: 5 givenname: Esther G. surname: Sinnema fullname: Sinnema, Esther G. – sequence: 6 givenname: Syuzanna R. orcidid: 0000-0003-2411-1250 surname: Harutyunyan fullname: Harutyunyan, Syuzanna R. email: s.harutyunyan@rug.nl |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36892214$$D View this record in MEDLINE/PubMed |
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Cites_doi | 10.1016/j.tetlet.2013.10.158 10.1126/science.1145295 10.1021/cs400685c 10.1002/chem.201602749 10.1002/anie.202112860 10.1039/c6gc00903d 10.1039/c5cc10185a 10.1021/ol2024339 10.1039/c6cs00031b 10.1016/j.ccr.2014.01.006 10.1016/j.ccr.2007.12.023 10.3762/bjoc.10.106 10.1002/adsc.200800277 10.1038/nature10702 10.1002/asia.201801061 10.1021/ol402627f 10.1039/c6cc00763e 10.1039/c0cc00925c 10.1039/c5cc09156j 10.1021/jacs.1c10756 10.1021/ol202480r 10.1021/acscatal.8b04787 10.1002/anie.201916076 10.1039/c4cc01610f 10.1002/anie.200700754 10.1002/chem.201406298 10.1021/jacs.1c02772 10.1055/s-0035-1560556 10.1039/b701677h 10.1021/cr020049i 10.1021/ja0449574 10.1002/ejoc.200500593 10.1002/anie.201702406 10.1039/d1sc06694c 10.1002/cjoc.202000160 10.1021/ja100606v 10.1021/jacs.0c09654 10.1002/anie.200700916 10.1073/pnas.0307152101 10.1021/ja0555163 10.1021/jacs.1c05649 10.1038/nrd1133 10.1039/c8cc05890c 10.1021/ol402351c 10.1021/cr100218m 10.1021/acscatal.6b02290 10.1007/978-1-4613-3623-5 10.1002/9783527630639 10.1021/om990882e 10.1039/C6CS00031B 10.1039/C4CC01610F 10.1039/B701677H 10.1039/C5CC09156J 10.1039/C6GC00903D 10.1039/C6CC00763E 10.1002/anie.202111137 10.1039/C5CC10185A 10.1002/9781118299715 10.1039/C8CC05890C 10.1039/D1SC06694C |
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Keywords | DIARYLPHOSPHINES CATALYSIS ALKENES DIPHOSPHINES LIGANDS PHOSPHINES 1,4-ADDITION ALKYNES |
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References | Valeur, E (WOS:000264374600019) 2009; 38 Wu, Z.-H. (000948711200001.39) 1000; 2021 van Leeuwen, P. W. N. M. (000948711200001.8) 2014 Sadow, AD (WOS:000225083700012) 2004; 126 Glueck, DS (WOS:000259897800003) 2008; 252 Gilheany, D. G. (000948711200001.2) 1990; 1 Moglie, Y (WOS:000383999300011) 2016; 18 Wang, CY (WOS:000643591600017) 2021; 143 Ibrahem, I (WOS:000258503600030) 2008; 350 Yue, WJ (WOS:000526818900013) 2020; 59 Bray, BL (WOS:000183713400020) 2003; 2 Chew, RJ (WOS:000350760000043) 2015; 21 Di Giuseppe, A (WOS:000374035800012) 2016; 52 Coles, NT (WOS:000444483700010) 2018; 54 Dutartre, M (WOS:000385181300010) 2016; 45 Maiti, R (WOS:000715328100001) 2021; 60 Li, YB (WOS:000595544800042) 2020; 142 Espinal-Viguri, M (WOS:000387306100072) 2016; 6 Sadeer, A (WOS:000446428900013) 2018; 13 Ding, BQ (WOS:000326615100021) 2013; 15 Itazaki, M (WOS:000370573400019) 2016; 52 Carlone, A (WOS:000247500600017) 2007; 46 Xie, JH (WOS:000288820600013) 2011; 111 Sadow, AD (WOS:000233759200052) 2005; 127 Kamer, P. C. J. (000948711200001.6) 2012 Lu, JZ (WOS:000326320200026) 2013; 15 Yang, XY (WOS:000372175700023) 2016; 52 Chen, YR (WOS:000296212200030) 2011; 13 Widegren, MB (WOS:000400755800030) 2017; 56 Feng, JJ (WOS:000276991700014) 2010; 132 Wauters, I (WOS:000335520200001) 2014; 10 Lu, ZW (WOS:000458707000069) 2019; 9 Chen, YR (WOS:000330153000003) 2014; 55 Tang, WJ (WOS:000184821500013) 2003; 103 Blaser, H. U. (000948711200001.9) 1983 Ibrahem, I (WOS:000247500600018) 2007; 46 Rosenberg, L (WOS:000328231400021) 2013; 3 Pfaltz, A (WOS:000220978000008) 2004; 101 Wei, Y (WOS:000562866000001) 2020; 38 Huang, YH (WOS:000282476600020) 2010; 46 Koshti, V (WOS:000332804700003) 2014; 265 Huang, YH (WOS:000296212200040) 2011; 13 Borner, A. (000948711200001.5) 2008; 1-3 Bange, CA (WOS:000383758200004) 2016; 22 Enders, D (WOS:000234237500002) 2006; 2006 Liu, XT (WOS:000684586600005) 2021; 143 Pullarkat, SA (WOS:000369749600002) 2016; 48 Gunanathan, C (WOS:000248624500036) 2007; 317 Pérez, JM (WOS:000750743100053) 2021; 143 Ge, L (WOS:000744556600001) 2022; 13 Chew, RJ (WOS:000339469900037) 2014; 50 Pattabiraman, VR (WOS:000298318000051) 2011; 480 Kovacik, I (WOS:000086082900002) 2000; 19 ref3/cit3 ref13/cit13a ref13/cit13b ref13/cit13c ref13/cit13d ref12/cit12b ref12/cit12a ref2/cit2 ref16/cit16c ref16/cit16b ref16/cit16a ref7/cit7f ref7/cit7e ref7/cit7d ref16/cit16d ref7/cit7c ref7/cit7b ref7/cit7a Kamer P. C. J. (ref4/cit4c) 2012 van Leeuwen P. W. N. M. (ref5/cit5a) 2014 ref5/cit5d ref10/cit10l ref6/cit6 ref10/cit10h ref10/cit10i ref10/cit10j ref10/cit10k ref10/cit10d ref9/cit9b ref10/cit10e ref9/cit9a ref10/cit10f ref11/cit11 ref10/cit10g ref8/cit8a ref10/cit10a ref8/cit8c ref10/cit10b ref8/cit8b ref10/cit10c ref8/cit8e ref8/cit8d ref8/cit8g ref8/cit8f ref8/cit8h Pignolet L. M. (ref5/cit5c) 1983 ref4/cit4a ref14/cit14a ref14/cit14b ref15/cit15 Blaser H. U. (ref5/cit5b) 2010 ref4/cit4d ref1/cit1 Borner A. (ref4/cit4b) 2008; 1 |
References_xml | – volume: 55 start-page: 595 year: 2014 ident: WOS:000330153000003 article-title: NHC-copper-catalyzed asymmetric 1,4-addition of diarylphosphines to α,β-unsaturated ketones publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2013.10.158 contributor: fullname: Chen, YR – volume: 317 start-page: 790 year: 2007 ident: WOS:000248624500036 article-title: Direct synthesis of amides from alcohols and amines with liberation of H2 publication-title: SCIENCE doi: 10.1126/science.1145295 contributor: fullname: Gunanathan, C – volume: 3 start-page: 2845 year: 2013 ident: WOS:000328231400021 article-title: Mechanisms of Metal-Catalyzed Hydrophosphination of Alkenes and Alkynes publication-title: ACS CATALYSIS doi: 10.1021/cs400685c contributor: fullname: Rosenberg, L – volume: 22 start-page: 12598 year: 2016 ident: WOS:000383758200004 article-title: Challenges in Catalytic Hydrophosphination publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201602749 contributor: fullname: Bange, CA – volume: 1-3 year: 2008 ident: 000948711200001.5 publication-title: Phosphorus Ligands in Asymmetric Catalysis contributor: fullname: Borner, A. – volume: 60 start-page: 26616 year: 2021 ident: WOS:000715328100001 article-title: Carbene-Catalyzed Enantioselective Hydrophosphination of α-Bromoenals to Prepare Phosphine-Containing Chiral Molecules publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.202112860 contributor: fullname: Maiti, R – volume: 18 start-page: 4896 year: 2016 ident: WOS:000383999300011 article-title: Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes publication-title: GREEN CHEMISTRY doi: 10.1039/c6gc00903d contributor: fullname: Moglie, Y – volume: 52 start-page: 3163 year: 2016 ident: WOS:000370573400019 article-title: Synthesis of vinylphosphines and unsymmetric diphosphines: iron-catalyzed selective hydrophosphination reaction of alkynes and vinylphosphines with secondary phosphines publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c5cc10185a contributor: fullname: Itazaki, M – volume: 2021 year: 1000 ident: 000948711200001.39 article-title: Cobalt-Catalysed Asymmetric Addition and Alkylation of Secondary Phosphine Oxides for the Synthesis of PStereogenic Compounds publication-title: Angew. Chem., Int. Ed. contributor: fullname: Wu, Z.-H. – volume: 13 start-page: 5824 year: 2011 ident: WOS:000296212200030 article-title: Palladium-Catalyzed 1,4-Addition of Diarylphosphines to α,β-Unsaturated Aldehydes publication-title: ORGANIC LETTERS doi: 10.1021/ol2024339 contributor: fullname: Chen, YR – volume: 45 start-page: 5771 year: 2016 ident: WOS:000385181300010 article-title: Applications and stereoselective syntheses of P-chirogenic phosphorus compounds publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c6cs00031b contributor: fullname: Dutartre, M – volume: 265 start-page: 52 year: 2014 ident: WOS:000332804700003 article-title: Contemporary avenues in catalytic P-H bond addition reaction: A case study of hydrophosphination publication-title: COORDINATION CHEMISTRY REVIEWS doi: 10.1016/j.ccr.2014.01.006 contributor: fullname: Koshti, V – volume: 19 start-page: 950 year: 2000 ident: WOS:000086082900002 article-title: Pt(Me-Duphos)-catalyzed asymmetric hydrophosphination of activated olefins: Enantioselective synthesis of chiral phosphines publication-title: ORGANOMETALLICS contributor: fullname: Kovacik, I – volume: 252 start-page: 2171 year: 2008 ident: WOS:000259897800003 article-title: Applications of 31P NMR spectroscopy in development of M(Duphos)-catalyzed asymmetric synthesis of P-stereogenic phosphines (M = Pt or Pd) publication-title: COORDINATION CHEMISTRY REVIEWS doi: 10.1016/j.ccr.2007.12.023 contributor: fullname: Glueck, DS – volume: 10 start-page: 1064 year: 2014 ident: WOS:000335520200001 article-title: Preparation of phosphines through C-P bond formation publication-title: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY doi: 10.3762/bjoc.10.106 contributor: fullname: Wauters, I – volume: 350 start-page: 1875 year: 2008 ident: WOS:000258503600030 article-title: Organocatalytic asymmetric hydrophosphination of α,β-unsaturated aldehydes:: Development, mechanism and DFT calculations publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.200800277 contributor: fullname: Ibrahem, I – volume: 480 start-page: 471 year: 2011 ident: WOS:000298318000051 article-title: Rethinking amide bond synthesis publication-title: NATURE doi: 10.1038/nature10702 contributor: fullname: Pattabiraman, VR – volume: 13 start-page: 2829 year: 2018 ident: WOS:000446428900013 article-title: Desymmetrization of Achiral Heterobicyclic Alkenes through Catalytic Asymmetric Hydrophosphination publication-title: CHEMISTRY-AN ASIAN JOURNAL doi: 10.1002/asia.201801061 contributor: fullname: Sadeer, A – year: 2012 ident: 000948711200001.6 publication-title: Phosphorus(III) Ligands in Homogeneous Catalysis contributor: fullname: Kamer, P. C. J. – volume: 15 start-page: 5476 year: 2013 ident: WOS:000326615100021 article-title: P-Stereogenic PCP Pincer-Pd Complexes: Synthesis and Application in Asymmetric Addition of Diarylphosphines to Nitroalkenes publication-title: ORGANIC LETTERS doi: 10.1021/ol402627f contributor: fullname: Ding, BQ – volume: 52 start-page: 4211 year: 2016 ident: WOS:000372175700023 article-title: The synthesis and efficient one-pot catalytic "self-breeding'' of asymmetrical NC(sp3)E-hybridised pincer complexes publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c6cc00763e contributor: fullname: Yang, XY – volume: 46 start-page: 6950 year: 2010 ident: WOS:000282476600020 article-title: Palladium(II)-catalyzed asymmetric hydrophosphination of enones: efficient access to chiral tertiary phosphines publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c0cc00925c contributor: fullname: Huang, YH – volume: 52 start-page: 5554 year: 2016 ident: WOS:000374035800012 article-title: Double hydrophosphination of alkynes promoted by rhodium: the key role of an N-heterocyclic carbene ligand publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c5cc09156j contributor: fullname: Di Giuseppe, A – year: 1983 ident: 000948711200001.9 publication-title: Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions; Wiley-VCH: with Metal Phosphine Complexes contributor: fullname: Blaser, H. U. – volume: 143 start-page: 20071 year: 2021 ident: WOS:000750743100053 article-title: Manganese(I)-Catalyzed H-P Bond Activation via Metal-Ligand Cooperation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.1c10756 contributor: fullname: Pérez, JM – volume: 13 start-page: 5862 year: 2011 ident: WOS:000296212200040 article-title: Direct Synthesis of Chiral Tertiary Diphosphines via Pd(II)-Catalyzed Asymmetric Hydrophosphination of Dienones publication-title: ORGANIC LETTERS doi: 10.1021/ol202480r contributor: fullname: Huang, YH – volume: 1 start-page: 151 year: 1990 ident: 000948711200001.2 publication-title: The Chemistry of Organophosphorus Compounds contributor: fullname: Gilheany, D. G. – volume: 9 start-page: 1457 year: 2019 ident: WOS:000458707000069 article-title: Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis publication-title: ACS CATALYSIS doi: 10.1021/acscatal.8b04787 contributor: fullname: Lu, ZW – volume: 59 start-page: 7057 year: 2020 ident: WOS:000526818900013 article-title: Rapid Synthesis of Chiral 1,2-Bisphosphine Derivatives through Copper(I)-Catalyzed Asymmetric Conjugate Hydrophosphination publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201916076 contributor: fullname: Yue, WJ – volume: 50 start-page: 8768 year: 2014 ident: WOS:000339469900037 article-title: Enantioselective phospha-Michael addition of diarylphosphines to β,γ-unsaturated α-ketoesters and amides publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c4cc01610f contributor: fullname: Chew, RJ – volume: 46 start-page: 4504 year: 2007 ident: WOS:000247500600017 article-title: Organocatalytic asymmetric hydrophosphination of α,β-Unsaturated aldehydes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200700754 contributor: fullname: Carlone, A – volume: 21 start-page: 4800 year: 2015 ident: WOS:000350760000043 article-title: Pd-Catalyzed Enantiodivergent and Regiospecific phospha-Michael Addition of Diphenylphosphine to 4-oxo-Enamides: Efficient Access to Chiral Phosphinocarboxamides and Their Analogues publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201406298 contributor: fullname: Chew, RJ – volume: 143 start-page: 5685 year: 2021 ident: WOS:000643591600017 article-title: Asymmetric Synthesis of P-Stereogenic Secondary Phosphine-Boranes by an Unsymmetric Bisphosphine Pincer-Nickel Complex publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.1c02772 contributor: fullname: Wang, CY – volume: 48 start-page: 493 year: 2016 ident: WOS:000369749600002 article-title: Recent Progress in Palladium-Catalyzed Asymmetric Hydrophosphination publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-0035-1560556 contributor: fullname: Pullarkat, SA – volume: 38 start-page: 606 year: 2009 ident: WOS:000264374600019 article-title: Amide bond formation: beyond the myth of coupling reagents publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b701677h contributor: fullname: Valeur, E – volume: 103 start-page: 3029 year: 2003 ident: WOS:000184821500013 article-title: New chiral phosphorus ligands for enantioselective hydrogenation publication-title: CHEMICAL REVIEWS doi: 10.1021/cr020049i contributor: fullname: Tang, WJ – volume: 126 start-page: 14704 year: 2004 ident: WOS:000225083700012 article-title: Nickel(II)-catalyzed highly enantioselective hydrophosphination of methacrylonitrile publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0449574 contributor: fullname: Sadow, AD – volume: 2006 start-page: 29 year: 2006 ident: WOS:000234237500002 article-title: The phospha-Michael addition in organic synthesis publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.200500593 contributor: fullname: Enders, D – year: 2014 ident: 000948711200001.8 publication-title: Homogeneous Catalysts: Activity-Stability-Deactivation contributor: fullname: van Leeuwen, P. W. N. M. – volume: 56 start-page: 5825 year: 2017 ident: WOS:000400755800030 article-title: A Highly Active Manganese Catalyst for Enantioselective Ketone and Ester Hydrogenation publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201702406 contributor: fullname: Widegren, MB – volume: 13 start-page: 1307 year: 2022 ident: WOS:000744556600001 article-title: Manganese(i)-catalyzed access to 1,2-bisphosphine ligands publication-title: CHEMICAL SCIENCE doi: 10.1039/d1sc06694c contributor: fullname: Ge, L – volume: 38 start-page: 1395 year: 2020 ident: WOS:000562866000001 article-title: Asymmetric Reactions Catalyzed by Chiral Tertiary Phosphines publication-title: CHINESE JOURNAL OF CHEMISTRY doi: 10.1002/cjoc.202000160 contributor: fullname: Wei, Y – volume: 132 start-page: 5562 year: 2010 ident: WOS:000276991700014 article-title: Palladium-Catalyzed Asymmetric Addition of Diarylphosphines to Enones toward the Synthesis of Chiral Phosphines publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja100606v contributor: fullname: Feng, JJ – volume: 142 start-page: 20098 year: 2020 ident: WOS:000595544800042 article-title: Copper(I)-Catalyzed Asymmetric 1,4-Conjugate Hydrophosphination of α,β-Unsaturated Amides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.0c09654 contributor: fullname: Li, YB – volume: 46 start-page: 4507 year: 2007 ident: WOS:000247500600018 article-title: Enantioselective organocatalytic hydrophosphination of α,β-unsaturated aldehydes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200700916 contributor: fullname: Ibrahem, I – volume: 101 start-page: 5723 year: 2004 ident: WOS:000220978000008 article-title: Design of chiral ligands for asymmetric catalysis:: From C2-symmetric P,P- and N,N-ligands to sterically and electronically nonsymmetrical. P,N-ligands publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA doi: 10.1073/pnas.0307152101 contributor: fullname: Pfaltz, A – volume: 127 start-page: 17012 year: 2005 ident: WOS:000233759200052 article-title: Enantioselective addition of secondary phosphines to methacrylonitrile: Catalysis and mechanism publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0555163 contributor: fullname: Sadow, AD – volume: 143 start-page: 11309 year: 2021 ident: WOS:000684586600005 article-title: Ni-Catalyzed Asymmetric Hydrophosphination of Unactivated Alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.1c05649 contributor: fullname: Liu, XT – volume: 2 start-page: 587 year: 2003 ident: WOS:000183713400020 article-title: Large-scale manufacture of peptide therapeutics by chemical synthesis publication-title: NATURE REVIEWS DRUG DISCOVERY doi: 10.1038/nrd1133 contributor: fullname: Bray, BL – volume: 54 start-page: 10443 year: 2018 ident: WOS:000444483700010 article-title: 1,1-Diphosphines and divinylphosphines via base catalyzed hydrophosphination publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c8cc05890c contributor: fullname: Coles, NT – volume: 15 start-page: 5016 year: 2013 ident: WOS:000326320200026 article-title: Palladium-Catalyzed Asymmetric Addition of Diarylphosphines to α,β-Unsaturated Sulfonic Esters for the Synthesis of Chiral Phosphine Sulfonate Compounds publication-title: ORGANIC LETTERS doi: 10.1021/ol402351c contributor: fullname: Lu, JZ – volume: 111 start-page: 1713 year: 2011 ident: WOS:000288820600013 article-title: Transition Metal-Catalyzed Enantioselective Hydrogenation of Enamines and Imines publication-title: CHEMICAL REVIEWS doi: 10.1021/cr100218m contributor: fullname: Xie, JH – volume: 6 start-page: 7892 year: 2016 ident: WOS:000387306100072 article-title: Hydrophosphination of Unactivated Alkenes and Alkynes Using Iron(II): Catalysis and Mechanistic Insight publication-title: ACS CATALYSIS doi: 10.1021/acscatal.6b02290 contributor: fullname: Espinal-Viguri, M – ident: ref8/cit8b doi: 10.1002/chem.201602749 – ident: ref10/cit10c doi: 10.1021/ol202480r – ident: ref6/cit6 doi: 10.3762/bjoc.10.106 – ident: ref16/cit16a doi: 10.1038/nrd1133 – ident: ref8/cit8g doi: 10.1021/jacs.0c09654 – volume-title: Homogeneous Catalysis with Metal Phosphine Complexes year: 1983 ident: ref5/cit5c doi: 10.1007/978-1-4613-3623-5 contributor: fullname: Pignolet L. M. – volume-title: Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions year: 2010 ident: ref5/cit5b doi: 10.1002/9783527630639 contributor: fullname: Blaser H. U. – ident: ref9/cit9a doi: 10.1021/om990882e – ident: ref10/cit10h doi: 10.1002/chem.201406298 – ident: ref12/cit12a doi: 10.1016/j.tetlet.2013.10.158 – ident: ref8/cit8f doi: 10.1021/jacs.1c05649 – ident: ref7/cit7d doi: 10.1021/acscatal.6b02290 – ident: ref1/cit1 doi: 10.1039/C6CS00031B – ident: ref8/cit8a doi: 10.1021/cs400685c – volume: 1 volume-title: Phosphorus Ligands in Asymmetric Catalysis year: 2008 ident: ref4/cit4b contributor: fullname: Borner A. – ident: ref16/cit16d doi: 10.1126/science.1145295 – ident: ref4/cit4d doi: 10.1021/cr100218m – ident: ref12/cit12b doi: 10.1002/anie.201916076 – volume-title: Homogeneous Catalysts: Activity-Stability-Deactivation year: 2014 ident: ref5/cit5a contributor: fullname: van Leeuwen P. W. N. M. – ident: ref10/cit10k doi: 10.1021/acscatal.8b04787 – ident: ref8/cit8h doi: 10.1002/ejoc.200500593 – ident: ref10/cit10e doi: 10.1021/ol402627f – ident: ref10/cit10b doi: 10.1021/ja100606v – ident: ref16/cit16b doi: 10.1038/nature10702 – ident: ref10/cit10d doi: 10.1021/ol2024339 – ident: ref10/cit10g doi: 10.1039/C4CC01610F – ident: ref16/cit16c doi: 10.1039/B701677H – ident: ref2/cit2 – ident: ref7/cit7f doi: 10.1039/C5CC09156J – ident: ref3/cit3 doi: 10.1002/cjoc.202000160 – ident: ref8/cit8d doi: 10.1021/ja0449574 – ident: ref7/cit7a doi: 10.1039/C6GC00903D – ident: ref11/cit11 doi: 10.1021/jacs.1c02772 – ident: ref7/cit7c doi: 10.1016/j.ccr.2014.01.006 – ident: ref13/cit13c doi: 10.1002/adsc.200800277 – ident: ref14/cit14a doi: 10.1021/jacs.1c10756 – ident: ref10/cit10i doi: 10.1039/C6CC00763E – ident: ref13/cit13a doi: 10.1002/anie.200700754 – ident: ref15/cit15 doi: 10.1002/anie.201702406 – ident: ref13/cit13b doi: 10.1002/anie.200700916 – ident: ref5/cit5d doi: 10.1073/pnas.0307152101 – ident: ref8/cit8e doi: 10.1021/ja0555163 – ident: ref10/cit10a doi: 10.1039/c0cc00925c – ident: ref10/cit10l doi: 10.1002/anie.202111137 – ident: ref4/cit4a doi: 10.1021/cr020049i – ident: ref8/cit8c doi: 10.1055/s-0035-1560556 – ident: ref9/cit9b doi: 10.1016/j.ccr.2007.12.023 – ident: ref7/cit7e doi: 10.1039/C5CC10185A – ident: ref13/cit13d doi: 10.1002/anie.202112860 – volume-title: Phosphorus(III) Ligands in Homogeneous Catalysis year: 2012 ident: ref4/cit4c doi: 10.1002/9781118299715 contributor: fullname: Kamer P. C. J. – ident: ref10/cit10j doi: 10.1002/asia.201801061 – ident: ref10/cit10f doi: 10.1021/ol402351c – ident: ref7/cit7b doi: 10.1039/C8CC05890C – ident: ref14/cit14b doi: 10.1039/D1SC06694C |
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Snippet | Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H–P bond... Here we report catalytic asymmetric hydrophosphi-nation of a,P-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H-P bond... Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H-P bond... Here we report catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst. Through H–P bond... |
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SubjectTerms | Chemistry Chemistry, Organic Letter Physical Sciences Science & Technology |
Title | Manganese(I)-Catalyzed Asymmetric Hydrophosphination of α,β‑Unsaturated Carbonyl Derivatives |
URI | http://dx.doi.org/10.1021/acs.orglett.2c04256 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000948711200001 https://www.ncbi.nlm.nih.gov/pubmed/36892214 https://search.proquest.com/docview/2785201178 https://pubmed.ncbi.nlm.nih.gov/PMC10028696 |
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