Trimethylsilyl triflate promoted addition of allyltributylstannane to aldonitrones; One-pot synthesis of 5-iodomethylisoxazolidines

被引：14
|
作者：
Gianotti, M [1 ]
Lombardo, M [1 ]
Trombini, C [1 ]
机构：
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 12期
关键词：
D O I：
10.1016/S0040-4039(97)10862-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The trimethylsilyl triflate promoted allylation of nitrones with allyltributylstannane affords O-silylated hydroxylamines in high yield; when the crude reaction mixture is quenched with N-iodosuccinimide, 5-iodomethylisoxazolidines are formed in excellent yields. The overall one-pot two-step process represents a valuable improvement in terms of time, cost and overall yield with respect to the previously reported three stage procedure involving nitrone allylation, hydroxylamine O-silylation, and iodocyclisation. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1643 / 1646
页数：4
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