RING-OPENING OF ISOXAZOLIDINE NUCLEUS - COMPETITIVE FORMATION OF ALPHA,BETA-ENONES AND TETRAHYDRO-1,3-OXAZINES

被引：25
作者：
CASUSCELLI, F
CHIACCHIO, U
RESCIFINA, A
ROMEO, R
ROMEO, G
TOMMASINI, S
UCCELLA, N
机构：
[1] UNIV CATANIA,DIPARTIMENTO SCI CHIM,I-95125 CATANIA,ITALY
[2] UNIV CALABRIA,DIPARTIMENTO CHIM,I-87036 ARCAVACATA,ITALY
来源：
TETRAHEDRON | 1995年 / 51卷 / 10期
关键词：
D O I：
10.1016/0040-4020(95)00030-C
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of isoxazolidine derivatives with methyl iodide, followed by simple heating with aqueous NaOH, gives rise to a competitive formation of alpha,beta-enones and tetahydro-1,3-oxazines. The ring-opening process is controlled by the stereochemistry of H-5 which represents the driving factor of two competitive reaction routes.
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收藏
页码：2979 / 2990
页数：12
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