The first catalytic asymmetric addition of dialkylzincs to α-ketoesters

被引：86

作者：

DiMauro, EF ^{[1
]}

Kozlowski, MC ^{[1
]}

机构：

[1] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 22期

关键词：

D O I：

10.1021/ol026315w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic The first catalytic, enantioselective addition of organozinc reagents to alpha-ketoesters is described. Modular bifunctional salen catalysts that contain Lewis acid and Lewis base activating groups accelerate the carbonyl addition to a much greater extent than the competing carbonyl reduction. alpha-Hydroxyesters containing new quaternary stereogenic centers are obtained in high yield and moderate enantiomeric excess. Enrichment to 98% ee can be effected by recrystallization of the corresponding alpha-hydroxy acid.

引用

页码：3781 / 3784

页数：4

共 36 条

[1] ASYMMETRIC ALKYLATION OF AN ALPHA-KETO ESTER WITH CHIRAL LITHIUM ALKOXY-TRIBUTYLALUMINATES [J].

ABENHAIM, D ;

BOIREAU, G ;

SABOURAULT, B .

TETRAHEDRON LETTERS, 1980, 21 (32) :3043-3046

[2] DIASTEREOSELECTIVE ADDITION OF ORGANOMETALLICS TO ALPHA-KETO ESTERS BEARING CHIRO-INOSITOL DERIVATIVES AS CHIRAL AUXILIARIES [J].

AKIYAMA, T ;

NISHIMOTO, H ;

ISHIKAWA, K ;

OZAKI, S .

CHEMISTRY LETTERS, 1992, (03) :447-450

[3]

[Anonymous], 1999, Comprehensive Asymmetric Catalysis

[4] Highly diastereoselective reduction and alkylation of (1R,2S)-trans-2-phenylcyclohexanol phenylglyoxylate and pyruvate using hindered hydrides and alkyl aluminates [J].

Boireau, G ;

Deberly, A ;

Loupy, A ;

Monteux, D .

TETRAHEDRON LETTERS, 1999, 40 (38) :6919-6922

[5]

Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO

[6]

2-V

[7]

Coppola G.M., 1997, ALPHA HYDROXY ACIDS

[8]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO

[9]

2-V

[10] Optimization of asymmetric catalysts using achiral ligands: Metal geometry-induced ligand asymmetry [J].

Davis, TJ ;

Balsells, J ;

Carroll, PJ ;

Walsh, PJ .

ORGANIC LETTERS, 2001, 3 (14) :2161-2164

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