Highly Diastereo- and Enantioselective Synthesis of Monodifferentiated syn-1,2-Diol Derivatives through Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution

被引：62

作者：

Cartigny, Damien ^{[1
]}

Puentener, Kurt ^{[2
]}

Ayad, Tahar ^{[1
]}

Scalone, Michelangelo ^{[2
]}

Ratovelomanana-Vidal, Virginie ^{[1
]}

机构：

[1] ENSCP Chim ParisTech, Lab Charles Friedel, UMR 7223, F-75231 Paris 05, France

[2] F Hoffmann La Roche & Cie AG, Proc Res & Synth CoE Catalysis, CH-4070 Basel, Switzerland

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 17期

关键词：

BETA-KETO-ESTERS; LEWIS-BASE ACTIVATION; ALPHA-AMINO; STEREOSELECTIVE-SYNTHESIS; HYDROXY ESTERS; CATALYSTS; ACIDS; LIGANDS; COMPLEX; ROUTE;

D O I：

10.1021/ol101451s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantio- and diastereoselective approach to alpha-alkoxy-substituted syn-beta-hydroxyesters through highly efficient catalytic asymmetric transfer hydrogenation via dynamic kinetic resolution reactions from the corresponding racemic beta-ketoesters is described. In this atom-economical process, two contiguous stereogenic centers are generated simultaneously with an excellent diastereoselectivity (up to 99/1) and enantioselectivity (up to 99%), allowing a rapid access to a wide variety of aromatic and heteroaromatic monodifferentiated syn-1,2-diols.

引用

页码：3788 / 3791

页数：4

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