SEQUENTIAL DIASTEREOSELECTIVE ADDITION AND ALLYLIC AZIDE ISOMERIZATION OF SYN-ALPHA-AZIDO-BETA-(DIMETHYLPHENYLSILYL)-(E)-HEX-4-ENOATES AND ANTI-ALPHA-AZIDO-BETA-(DIMETHYLPHENYLSILYL)-(E)-HEX-4-ENOATES WITH ACETALS - ASYMMETRIC-SYNTHESIS OF GAMMA-HYDROXY-ALPHA-AMINO ACID SYNTHONS

被引:41
作者
PANEK, JS
YANG, M
MULER, I
机构
[1] Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, Boston
关键词
D O I
10.1021/jo00041a002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
syn- and anti-methyl alpha-azido-beta-(dimethylphenylsilyl)-(E)-hex-4-enoates (2R,3R)-1a and (2S,3R)-1b undergo highly diastereo- and enantioselective addition reactions with oxonium ions catalyzed by the action of trimethylsilyl trifluoromethanesulfonate (TMSOTf) to generate alpha-azido-beta,gamma-unsaturated esters 2, with well-defined 1,4- and 1,5-stereochemical relationships, and a subsequent stereospecific allylic azide isomerization generated 1,3-azido ethers 3, synthetic equivalents of gamma-hydroxy-alpha-amino acids.
引用
收藏
页码:4063 / 4064
页数:2
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