Synthesis and reactions of some optically active epoxides formally derived from tertiary allylic alcohols

被引：6

作者：

Bickley, JF ^{[1
]}

Gillmore, AT ^{[1
]}

Roberts, SM ^{[1
]}

Skidmore, J ^{[1
]}

Steiner, A ^{[1
]}

机构：

[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 09期

关键词：

D O I：

10.1039/b008275i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The epoxyketones 2, 3 and 7-9 reacted with Grignard reagents in a highly stereocontrolled manner to give the epoxyalcohols 20, 4-6 and 11-13 in high yields. The epoxyalcohol 12 underwent a Payne rearrangement on base treatment to give the isomer 15 while epoxyalcohols 4, 5, 12 and 20 suffered ring-opening (with retention of configuration) using tin(IV) chloride to afford chlorodiols 18, 17, 19 and 21 respectively. On the other hand, the alcohols 4, 5 and 12 reacted with trialkylsilyl chlorides to furnish the chlorodiols 22, 24 and 23 respectively with inversion of configuration.

引用

页码：1109 / 1115

页数：7

共 20 条

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