Unexpected rearrangement in the heck cyclization of positional isomers of chiral 2,3-disubstituted perhydro-1,3-benzoxazines

被引：0

作者：

Pedrosa, R ^{[1
]}

Andrés, C ^{[1
]}

Iglesias, JM ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

SYNLETT | 2002年 / 02期

关键词：

cyclizations; Heck reaction; palladium; rearrangements;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular Heck cyclization on 2,3-disubstituted perhydro-1,3-benzoxazines, derived from (-)-8-amino menthol, easily proceeds at reflux of acetonitrile or DMF. The behavior of positional isomers was quite different. Reaction of 2-aryl-3-allyl perhydro-1,3-benzoxazines occurred as expected giving exclusively 6-exo cyclization products. On the contrary, regioisomeric 3-(iodobenzyl)-2-vinyl derivatives gave the normal cyclization compounds and rearranged 1,2-dihydroisoquinoline nucleus.

引用

页码：259 / 262

页数：4

共 39 条

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