Synthesis of (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal:: A potential building block for the asymmetric synthesis of non-natural amino acids

被引：13

作者：

Alías, M ^{[1
]}

Cativiela, C ^{[1
]}

Díaz-de-Villegas, MD ^{[1
]}

Gálvez, JA ^{[1
]}

Lapeña, Y ^{[1
]}

机构：

[1] Univ Zaragoza, CSIC, Inst Ciencia Mat Aragon, Fac Ciencias,Dept Quim Organ, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 49期

关键词：

amino acids and derivatives; asymmetric synthesis;

D O I：

10.1016/S0040-4020(98)00937-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound (S)-alpha-methylserinal acetonide has been efficiently prepared from (S)-alpha-methylserine, which is readily available in enantiomerically pure form by Curtius rearrangement of alpha,alpha-dialkyl 2-cyanoesters obtained by diastereoselective alkylation of (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate using methoxymethyl iodide or paraformaldehyde as electrophiles by an extension of our recently developed methodology for the synthesis of alpha,alpha-dialkylamino acids, (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：14963 / 14974

页数：12

共 31 条

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