New synthesis of isoxazolidines

被引：7

作者：

Malamas, MS

Palka, CL

机构：

[1] Department of Medicinal Chemistry, Wyeth-Ayerst Research, Inc., CN 8000, Princeton

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1996年 / 33卷 / 02期

关键词：

D O I：

10.1002/jhet.5570330241

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of 5-substituted isoxazolidines was developed by direct isoxazolidine ring formation of allylic hydroxylamines under acidic conditions. The cyclization process is an electrophilic S(N)1 type reaction. The formed carbocation intermediate is stabilized by electron rich groups (ie., phenyl). A moiety that mediates oxonium ion formation (i.e., para-methoxy) accelerates the rate of product formation.

引用

页码：475 / 478

页数：4

共 5 条

[1]

GRUNANGER P, 1991, CHEM HETEROCYCL COMP, V49, P649

[2]

HUGHES DL, 1992, MITSUNOBU REACTION O, P335

[3]

INGENDOH A, 1987, Patent No. 4678797

[4] RAPID CHROMATOGRAPHIC TECHNIQUE FOR PREPARATIVE SEPARATIONS WITH MODERATE RESOLUTION [J].