HETEROCONJUGATE ADDITION AT C-1 POSITION OF PYRANOSE DERIVATIVE, PSEUDOENANTIOMERIC METHODOLOGY FOR ASYMMETRIC INTRODUCTION

被引:24
作者
ISOBE, M
JIANG, YM
机构
[1] Laboratory of Organic Chemistry, School of Agricultural Sciences, Nagoya University, Chikusa, Nagoya
关键词
D O I
10.1016/0040-4039(94)02254-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new synthetic method providing both enantiomers by heteroconjugate addition strategy rs described for stereocontrolled synthesis of optically active compounds from sugar chirons. Preparation includes introduction of phenylthioacetylene, acidic epimerization via dicobalthexacarbonyl complex, hydrosilylation and oxidation. Addition of carbon nucleophiles to the heteroolefins extended at the C-1 position yielded the product with high stereoselectivity. Mode of addition was switchable via alpha- or beta-chelation control.
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页码:567 / 570
页数:4
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