α-Methylserinals as an access to α-methyl-β-hydroxyamino acids:: application in the synthesis of all stereoisomers of α-methylthreonine

被引：16

作者：

Avenoza, A ^{[1
]}

Busto, JH ^{[1
]}

Corzana, F ^{[1
]}

Peregrina, JM ^{[1
]}

Sucunza, D ^{[1
]}

Zurbano, MM ^{[1
]}

机构：

[1] Univ La Rioja, Dept Quim, Grp Sintesis Quim Rioja, CSIC,UA, E-26006 Logrono, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 04期

关键词：

D O I：

10.1016/j.tetasy.2003.12.001

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric synthesis of all stereoisomers of alpha-methylthreonine using a stereodivergent synthetic route starting from (S)- and (R)-N-Boc-N,O-isopropylidene-alpha-methylserinals is reported. The key step involves the asymmetric addition of methylmagnesium bromide to these aldehydes with a high level of asymmetric induction being observed. This methodology represents a powerful tool for the synthesis of different beta-substituted alpha-methylserines. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：719 / 724

页数：6

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