Highly diastereoselective synthesis of vinylcyclopropane derivatives with (-)-8-phenylmenthol as chiral auxiliary

被引：30

作者：

Ye, S ^{[1
]}

Tang, Y ^{[1
]}

Dai, LX ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 17期

关键词：

D O I：

10.1021/jo010121x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The silylated telluronium. allylide 4, generated in situ from the corresponding telluronium salt in the presence of LiTMP, reacted with (-)-8-phenylmenthyl alpha,beta -unsaturated esters to afford trans-2-silylvinyl-trans-3-substituted cyclopropyl esters with high diastereoselectivity in high yields. The absolute configuration was determined by chemical transformation. A mechanistic rationale is proposed.

引用

页码：5717 / 5722

页数：6

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