Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation

被引：152

作者：

Amatore, Muriel ^{[1
]}

Beeson, Teresa D. ^{[1
]}

Brown, Sean P. ^{[1
]}

MacMillan, David W. C. ^{[1
]}

机构：

[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 28期

关键词：

epoxidation; enantioselectivity; asymmetric catalysis; organocatalysis; HYDROLYTIC KINETIC RESOLUTION; HALOGENATION; ORGANOCATALYSIS; ACTIVATION; COMPLEXES; OLEFINS; KETONES;

D O I：

10.1002/anie.200901855

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Time for SOme MOre: For the first time SOMO (singly occupied molecular orbital) activation has been exploited to allow a new approach to the α-chlorination of aldehydes. This transformation can be readily implemented as part of a linchpin catalysis approach to the enantioselective production of terminal epoxides. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5121 / 5124

页数：4

共 36 条

[1] Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides
Annis, DA
Jacobsen, EN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) : 4147 - 4154
[2] [Anonymous], 1999, COMPREHENSIVE ASYMME
[3] Enantioselective organocatalysis using SOMO activation
Beeson, Teresa D.
Mastracchio, Anthony
Hong, Jun-Bae
Ashton, Kate
MacMillan, David W. C.
[J]. SCIENCE, 2007, 316 (5824) : 582 - 585
[4] Direct and enantioselective organocatalytic α-chlorination of aldehydes
Brochu, MP
Brown, SP
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) : 4108 - 4109
[5] Catalytic enantioselective diboration, disilation and silaboration: new opportunities for asymmetric synthesis
Burks, Heather E.
Morken, James P.
[J]. CHEMICAL COMMUNICATIONS, 2007, (45) : 4717 - 4725
[6] Mechanism and conditions for highly enantioselective epoxidation of α,β-enones using charge-accelerated catalysis by a rigid quaternary ammonium salt
Corey, EJ
Zhang, FY
[J]. ORGANIC LETTERS, 1999, 1 (08) : 1287 - 1290
[7] De Kimpe N., 1988, The Chemistry of alpha-Haloketones, alpha-Haloaldehydes and alphaHaloimines
[8] Recent developments in catalytic, asymmetric α-halogenation:: A new frontier in asymmetric catalysis
France, S
Weatherwax, A
Lectka, T
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (03) : 475 - 479
[9] Enantioselective Organo-Singly Occupied Molecular Orbital Catalysis: The Carbo-oxidation of Styrenes
Graham, Thomas H.
Jones, Casey M.
Jui, Nathan T.
MacMillan, David W. C.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) : 16494 - +
[10] Mechanistic investigation of the 2,5-diphenylpyrrolidine-catalyzed enantioselective α-chlorination of aldehydes
Halland, N
Lie, MA
Kjærsgaard, A
Marigo, M
Schiott, B
Jorgensen, KA
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (23) : 7083 - 7090

← 1 2 3 4 →