On the mechanism of base-induced rearrangements of epoxides to ketones:: a formal synthesis of (S)-physoperuvine

被引：30

作者：

Hodgson, DM ^{[1
]}

Robinson, LA ^{[1
]}

Jones, ML ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 49期

关键词：

epoxide; epoxidation; ketone; organolithium;

D O I：

10.1016/S0040-4039(99)01810-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective alpha-deprotonation-rearrangement of trans- and cis-5-silyloxycycloheptene oxides (trans-8 and cis-8) using organolithiums in the presence of(-)-sparteine 16 or (-)-alpha-isosparteine 17 to give predominantly 4-silyloxycycloheptanone [(R)-9 (up to 87% ee), a known intermediate in the synthesis of (S)-physoperuvine (10), and (S)-9 (up to 71% ee), respectively] is described; the results indicate an alpha-ring opening mechanism. (C) 1999 Elsevier Science Ltd, All rights reserved.

引用

页码：8637 / 8640

页数：4

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