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 42 条

[1] X=Y-ZH systems as potential 1,3-dipoles. Part 55: Cascade 1,3-azaprotio cyclotransfer-cycloaddition reactions between ketoximes and divinyl ketone
Dunn, PJ
Graham, AB
Grigg, R
Saba, IS
Thornton-Pett, M
TETRAHEDRON, 2002, 58 (38) : 7701 - 7713
[2] Tandem 1,3-azaprotio cyclotransfer-cycloaddition reactions between aldoximes and divinyl ketone.: The effect of oxime E/Z-isomerism on cycloaddition stereoselectivity
Dunn, PJ
Graham, AB
Grigg, R
Higginson, P
Saba, IS
CHEMICAL COMMUNICATIONS, 2000, (20) : 2033 - 2034
[3] X=Y-ZH systems as potential 1,3-dipoles. Part 57: Cascade 1,3-azaprotio cyclotransfer-cycloaddition reactions between aldoximes and divinyl ketone: remarkable rate enhancement and control of cycloaddition regiochemistry by Lewis acids
Dunn, PJ
Graham, AB
Grigg, R
Higginson, P
Thornton-Pett, M
TETRAHEDRON, 2002, 58 (38) : 7727 - 7733
[4] X=Y-ZH system as potential 1,3-dipoles. Part 59: Cascade 1,3-azaprotio cyclotransfer-1,3-dipolar cycloaddition (1,3-APT-1,3-DC) reactions of benzobicyclo[3.3.1]non-5-en-9-one oxime
Dondas, HA
Fishwick, CWG
Grigg, R
Thornton-Pett, M
TETRAHEDRON, 2003, 59 (50) : 9997 - 10007
[5] Tandem 1,3-azaprotio cyclotransfer-cycloaddition reactions between ketoximes and divinyl ketone or its equivalents: Lewis acid mediated rate enhancement and control of cycloaddition regioselectivity
Saba, IS
Frederickson, M
Grigg, R
Dunn, PJ
Levett, PC
TETRAHEDRON LETTERS, 1997, 38 (34) : 6099 - 6102
[6] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .37. GENERATION OF NITRONES FROM OXIMES - TANDEM INTRAMOLECULAR 1,3-AZAPROTIO CYCLOTRANSFER INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION REACTIONS - CLASS-4 PROCESSES
GRIGG, R
MARKANDU, J
SURENDRAKUMAR, S
THORNTONPETT, M
WARNOCK, WJ
TETRAHEDRON, 1992, 48 (47) : 10399 - 10422
[7] X=Y-ZH systems as potential 1,3-dipoles.: Part 53:: Sequential nucleophilic ring opening-1,3-dipolar cycloaddition reactions of Z-oxime anions with aziridines and dipolarophiles
Dondas, HA
Cummins, JE
Grigg, R
Thornton-Pett, M
TETRAHEDRON, 2001, 57 (37) : 7951 - 7964
[8] X=Y-ZH Systems as potential 1,3-dipoles.: Part 52:: Fused-ring forming electrophile induced oxime→nitrone→cycloaddition cascades
Dondas, HA
Grigg, R
Thibault, S
TETRAHEDRON, 2001, 57 (32) : 7035 - 7045
[9] X = Y-ZH systems as potential 1,3-dipoles - XLVI. Cascade 1,3-dipolar cycloaddition reactions of cephalosporin imines
Tetrahedron, 48 (13347):
[10] X = Y-ZH Systems as potential 1,3-dipoles. Part 47. Tandem nucleophilic substitution-1,3 dipolar cycloaddition reactions of oximes with epoxides and dipolarophiles
Tetrahedron, 38 (13165):

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