X=Y-ZH systems as potential 1,3-dipoles.: Part 56:: Cascade 1,3-azaprotio cyclotransfer-cycloaddition reactions between aldoximes and divinyl ketone:: the effect of oxime E/Z isomerism on cycloaddition stereoselectivity

被引：17
作者：
Blackwell, M
Dunn, PJ
Graham, AB
Grigg, R
Higginson, P
Saba, IS
Thornton-Pett, M
机构：
[1] Univ Leeds, Sch Chem, Mol Innovat Divers & Automated Synth Ctr, Leeds LS2 9JT, W Yorkshire, England
[2] Pfizer Ltd, Global Res & Dev UK, Sandwich CT13 9NJ, Kent, England
来源：
TETRAHEDRON | 2002年 / 58卷 / 38期
基金：
英国工程与自然科学研究理事会;
关键词：
aliphatic oximes; isomerism; cycloaddition;
D O I：
10.1016/S0040-4020(02)00835-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The cascade 1,3-azaprotiocyclotransfer (1,3-APT)-1,3-dipolar-cycloaddition (1,3-DC) reaction between aldoximes and divinyl ketone affords mixtures of exo and endo-isomers of substituted 1-aza-7-oxabicyclo[3,2,1]octan-4-ones, the ratio of which is dependent on the E/Z geometry of the starting oxime and its ability to isomerise under the thermal reaction conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：7715 / 7725
页数：11
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