Stereocontrolled α-alkylation of fully protected L-serine

被引：19

作者：

Brunner, M

Saarenketo, P

Straub, T

Rissanen, K

Koskinen, AMP

机构：

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

[2] Univ Jyvaskyla, Organ Chem Lab, SF-40351 Jyvaskyla, Finland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 18期

关键词：

amino acids; alkylation; diastereoselectivity; heterocycles; X-ray diffraction;

D O I：

10.1002/ejoc.200400207

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective alkylation of the (2S,4S) and (2R,4S) diastereomers of 3-tert-butyl 4-methyl 2-tert-butyl-1,3-oxazolidine-3,4-dicarboxylate (1a/b) is reported. Formation of both diastereomers of these oxazolidines was achieved by changing the order of protection steps, and their relative and absolute configurations were determined by NOESY spectroscopy. The use of the bulky ring substituent tBu together with Boc as the N-protecting group led to the exclusive formation of only one alkylated diastereomer. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

引用

收藏

页码：3879 / 3883

页数：5

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