N-Boc-alpha-tosylsarcosine ethyl ester: An alpha-amido sulfone for the regio- and stereoselective synthesis of protected gamma,delta-unsaturated N-methyl-alpha-amino acids by palladium-catalyzed nucleophilic substitution

被引：7

作者：

Alonso, DA ^{[1
]}

Costa, A ^{[1
]}

Najera, C ^{[1
]}

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,ALICANTE 03080,SPAIN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(97)10054-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Boc-alpha-tosylsarcosine ethyl ester (3) reacts under neutral conditions either with allylic carbonates or with vinyloxirane in the presence of a catalytic amount of Pd(PPh3)(4) and dppe (5 mol%) to give regio- and stereoselectively the corresponding allylated products 5 and 6, respectively. Reductive desulfonylation of these compounds with Mg-MeOH affords the corresponding protected gamma,delta-unsaturated N-methyl-alpha-amino acids 7 and 8. (C) 1997 Elsevier Science Ltd.

引用

页码：7943 / 7946

页数：4

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