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
收藏
页码：8637 / 8640
页数：4
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