Efficient asymmetric selenocyclizations of alkenyl oximes into cyclic nitrones and 1,2-oxazines promoted by sulfur containing diselenides

被引：45

作者：

Tiecco, M ^{[1
]}

Testaferri, L ^{[1
]}

Bagnoli, L ^{[1
]}

Purgatorio, V ^{[1
]}

Temperini, A ^{[1
]}

Marini, F ^{[1
]}

Santi, C ^{[1
]}

机构：

[1] Univ Perugia, Sez Chim Organ, Dipartimento Chim & Tecnol Farm, I-06123 Perugia, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 23期

关键词：

D O I：

10.1016/S0957-4166(02)00013-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Treatment of the di-2-[(1S)-1-(methylthio)ethyl]phenyl diselenide or of the di-2-methoxy-6-[(1S)-1-methylthio)ethyl]phenyl diselenide with bromine and silver triflate afforded the corresponding electrophilic selenylating triflates which were used in situ to promote the asymmetric selenocyclization of gamma-alkenyl oximes and delta-phenyl-gamma-alkenyl oximes. The course of these reactions and hence the structures of the cyclization products were dictated by the (E)- or (Z)-geometry of the starting oximes. The two types of cyclization products were either the cyclic nitrones or the 1,2-oxazines; in both cases the reactions proceeded with excellent yields. complete regioselectivity and good diastereoselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3297 / 3304

页数：8

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