Diastereoselective formation of highly functionalised α-substituted amino acid derivatives via aldol addition

被引：3

作者：

Brunner, M

Nissinen, M

Rissanen, K

Straub, T

Koskinen, AMP

机构：

[1] Aalto Univ, Organ Chem Lab, FIN-02150 Espoo, Finland

[2] Univ Jyvaskyla, Organ Chem Lab, FIN-40014 Jyu, Finland

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2005年 / 734卷 / 1-3期

关键词：

aldol; myriocin; diastereoselectivity;

D O I：

10.1016/j.molstruc.2004.09.020

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Highly diastereoselective aldol additions of (2R,4S)-3-tert-butyl 4-methyl 2-tert-butyloxazolidine-3,4-dicarboxylate (1) are reported. The utility of the highly substituted oxazolidines of type 1 for diastereoselective alpha-addition of the fully protected amino acid L-serine with achiral and chiral carbonyl compounds is demonstrated and the relative and absolute configuration of the aldol products are discussed on the basis of NOESY data and solid state structures of selected examples. The aldol products represent highly useful intermediates in the syntheses of sphingosine-related metabolites. (C) 2004 Elsevier B.V. All rights reserved.

引用

页码：177 / 182

页数：6

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