Enantiopure α-silyl-substituted α-hydroxyacetic acids using O-H insertion methodology and boron-based asymmetric reductions

被引：16

作者：

Bolm, C ^{[1
]}

Saladin, S ^{[1
]}

Classen, A ^{[1
]}

Kasyan, A ^{[1
]}

Veri, E ^{[1
]}

Raabe, G ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany

来源：

SYNLETT | 2005年 / 03期

关键词：

hydroxy acids; O-H insertion; dirbodium(II) acetate; diazo compounds; asymmetric borane reduction;

D O I：

10.1055/s-2005-862369

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two routes to optically active alpha-silyl-substituted alpha-hydroxyacetic acids are described. As a key step, the first utilizes O-H insertion reactions of (R)-and (S)-phenylethanol into benzyl 2-silyl-2-diazoacetates in the presence of [Rh-2(OAc)(4)]. Alternatively, asymmetric reductions of benzyl 2-silyl-2-oxoacetates using (R)Alpine-Boranee(R) afford the corresponding alpha-hydroxy esters with up to 91% ee.

引用

页码：461 / 464

页数：4

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