RING-OPENING OF ISOXAZOLIDINE NUCLEUS BY TRIMETHYL PHOSPHATE TREATMENT - FORMATION OF TERTIARY ALLYLIC ALCOHOLS VIA INTERMEDIATE 1,3-OXAZINIUM SALTS

被引：9

作者：

CHIACCHIO, U

LIGUORI, A

ROMEO, G

SINDONA, G

UCCELLA, N

机构：

[1] UNIV ARCAVACATA RENDE,DIPARTIMENTO CHIM,I-87036 ARCAVACATA,ITALY

[2] UNIV MESSINA,DIPARTIMENTO FARMACOCHIM,I-98168 MESSINA,ITALY

来源：

HETEROCYCLES | 1993年 / 36卷 / 04期

关键词：

D O I：

10.3987/COM-92-6239

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5,5-Disubstituted isoxazolidines undergo ring opening reaction, leading to tertiary allylic alcohols, by sequential treatment with trimethyl phosphate (TMP) and NaH. The reaction proceeds through sequence steps which involve an initial alkylation to isoxazolidinium intermediate, followed by ring expansion to tetrahydro-1,3-oxazine, further alkylation and a Hofmann-like elimination towards the final products promoted by NaH.

引用

页码：799 / 817

页数：19

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