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

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Thornton-Pett, M
TETRAHEDRON, 2001, 57 (06) : 1119 - 1128
[32] 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
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[33] X=Y-ZH systems as potential 1,3-dipoles .49. catalytic palladium (II) mediated oxime-nitrone-isoxazolidine cascades
Frederickson, M
Grigg, R
Markandu, J
ThorntonPett, M
Redpath, J
TETRAHEDRON, 1997, 53 (44) : 15051 - 15060
[34] X=Y-ZH Systems as potential 1,3-dipoles.: Part 54:: Stereo- and facially-selective formation of bridged bicyclic N-heterocycles via a sequential one-pot electrophile induced oxime→nitrone→cycloaddition sequence.: Multiplication of chirality
Dondas, HA
Grigg, R
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Thornton-Pett, M
TETRAHEDRON, 2002, 58 (29) : 5827 - 5836
[35] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .31. GENERATION OF NITRONES FROM OXIMES - BACKGROUND AND SCOPE OF THE TANDEM 1,2-PROTOTROPY-INTRAMOLECULAR CYCLOADDITION SEQUENCE
GRIGG, R
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[37] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .16. CYCLOPROPYL SUBSTITUTED AZOMETHINE YLIDES AS MECHANISTIC PROBES IN 1,3-DIPOLAR CYCLO-ADDITION REACTIONS
GRIGG, R
ARMSTRONG, WP
TETRAHEDRON, 1988, 44 (05) : 1523 - 1534
[38] X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .30. CYCLOADDITION OF ARYLIDENE IMINES OF ALPHA-AMINO ESTERS TO ACETYLENIC DIPOLAROPHILES AND PYRROLE FORMING REARRANGEMENTS
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[39] X=Y-ZH compounds as potential 1,3-dipoles. Part 64: Synthesis of highly substituted conformationally restricted and spiro nitropyrrolidines via Ag(I) catalysed azomethine ylide cycloadditions
Grigg, Ronald
Kilner, Colin
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de la Cierva, Cecilia Orgaz
Dondas, H. Ali
TETRAHEDRON, 2008, 64 (37) : 8974 - 8991
[40] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .34. GENERATION OF NITRONES FROM OXIMES - TANDEM MICHAEL ADDITION-1,3-DIPOLAR CYCLOADDITION REACTIONS - CLASS-2 PROCESSES UTILIZING BIFUNCTIONAL MICHAEL ACCEPTOR-DIPOLAROPHILE COMPONENTS
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