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

被引:41
作者
ARMSTRONG, P [1 ]
GRIGG, R [1 ]
HEANEY, F [1 ]
SURENDRAKUMAR, S [1 ]
WARNOCK, WJ [1 ]
机构
[1] UNIV LEEDS, SCH CHEM, LEEDS LS2 9JT, W YORKSHIRE, ENGLAND
关键词
D O I
10.1016/S0040-4020(01)87117-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-3, -4, -5, and -6-Alkenyl oximes react with electronegative olefins at the nitrogen atom via a Michael addition or ene-type process to generate the corresponding C-alkenyl nitrones which undergo an intramolecular cycloaddition. The cycloaddition can occur by one of two modes leading to either bridged- or fused-isoxazolidines. The latter is preferred in most cases except that of the C-(3-alkenyl) nitrone which gives exclusively the bridged-ring product and the C-(4-alkenyl)nitrones derived from N-allylpyrrole-2-carboxyaldehyde oxime which gives both bridged- and fused-ring isoxazolidines.
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页码:4495 / 4518
页数:24
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