A Powerful Chiral Counteranion Motif for Asymmetric Catalysis

被引：215

作者：

Garcia-Garcia, Pilar ^{[1
]}

Lay, Frank ^{[1
]}

Garcia-Garcia, Patricia ^{[1
]}

Rabalakos, Constantinos ^{[1
]}

List, Benjamin ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 24期

关键词：

disulfonimides; homogeneous catalysis; Mukaiyama aldol reaction; organocatalysis; ENANTIOSELECTIVE MUKAIYAMA-ALDOL; TRANSITION-METAL CATALYSIS; MANNICH-TYPE REACTION; DIELS-ALDER REACTION; LEWIS-ACID CATALYST; BRONSTED ACID; PHOSPHORIC-ACID; VERSATILE CATALYST; ACTIVATION; ALDEHYDES;

D O I：

10.1002/anie.200901768

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Room to swing a cat: A chiral disulfonimide has been designed as a powerful new motif for asymmetric catalysis. As a first illustration, a highly efficient and enantioselective Mukaiyama aldol reaction has been developed (see scheme). The actual catalyst is proposed to be an N-silyl imide which is generated in situ. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4363 / 4366

页数：4

共 41 条

[1] Phosphoric acid diesters as efficient catalysts for hydroaminations of nonactivated alkenes and an application to asymmetric hydroaminations [J].

Ackermann, Lutz ;

Altharnmer, Andreas .

SYNLETT, 2008, (07) :995-998

[2] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[3] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[4]

[Anonymous], 2006, ANGEW CHEM-GER EDIT

[5]

[Anonymous], 2008, ANGEW CHEM

[6]

[Anonymous], 2004, ANGEW CHEM INT EDIT

[7] o-Benzenedisulfonimide as a Soft, Efficient, and Recyclable Catalyst for the Acylation of Alcohols, Phenols, and Thiols under Solvent-Free Conditions: Advantages and Limitations [J].

Barbero, Margherita ;

Cadamuro, Silvano ;

Dughera, Stefano ;

Venturello, Paolo .

SYNTHESIS-STUTTGART, 2008, 22 (22) :3625-3632

[8]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[9]

Carreira E. M., 2009, CLASSICS STEREOSELEC

[10] CATALYTIC, ENANTIOSELECTIVE ALDOL ADDITIONS WITH METHYL AND ETHYL-ACETATE O-SILYL ENOLATES - A CHIRAL TRIDENTATE CHELATE AS A LIGAND FOR TITANIUM(IV) [J].

CARREIRA, EM ;

SINGER, RA ;

LEE, WS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8837-8838

← 1 2 3 4 5 →