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

页码：7715 / 7725

页数：11

共 25 条

[1] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .33. GENERATION OF NITRONES FROM OXIMES - TANDEM MICHAEL ADDITION-1,3-DIPOLAR CYCLOADDITION REACTIONS - CLASS-2 PROCESSES IN WHICH THE DIPOLAROPHILE IS LOCATED WITHIN THE OXIME [J].