A rapid approach to amino-acid derivatives by [2,3]-Stevens rearrangement

被引：0

作者：

Arboré, APA ^{[1
]}

Cane-Honeysett, DJ ^{[1
]}

Coldham, I ^{[1
]}

Middleton, ML ^{[1
]}

机构：

[1] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England

来源：

SYNLETT | 2000年 / 02期

关键词：

amines; amino acids; rearrangements; ylides; chirality transfer;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylation of amino-acid esters gives rise to intermediate quaternary ammonium salts, which undergo proton abstraction to give ylides and [2,3]-sigmatropic rearrangement. The resulting alpha-amino-acid derivatives can be subjected to N-deallylation to provide a rapid access to alpha-allyl-alpha-amino-esters. Using N-benzyl proline methyl ester, chirality transfer from carbon to nitrogen then back to carbon takes place.

引用

页码：236 / 238

页数：3

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