Regiocontrol in the 1,3-dipolar cycloaddition reactions of mesoionic compounds with acetylenic dipolarophiles.

被引：16
|
作者：
Coppola, BP [1 ]
Noe, MC [1 ]
Hong, SSK [1 ]
机构：
[1] UNIV MICHIGAN,DEPT CHEM,ANN ARBOR,MI 48109
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 41期
关键词：
D O I：
10.1016/S0040-4039(97)01761-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The regioselectivity of 1,3-dipolar cycloaddition reactions between mesoionic compounds with singly-tethered substituents is examined. The results with propiolate dipolarophiles are compared with other singly and doubly-tethered examples according to a model using an asynchronous, concerted transition state. The isolation and reaction of a novel, non-aryl substituted mesoionic compound 7 is reported. A regiodirected synthesis starting with N-(2-thiazolinyl)proline gives a complementary dihydropyrroline compared with the reaction between N-formylproline and alkyl propiolates. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：7159 / 7162
页数：4
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