Photosensitized intramolecular cyclization of furan and non-activated alkene: pathway switching by the substituent on the furan ring

被引：17

作者：

Arai, Noriyoshi ^{[1
]}

Tanaka, Koichiro ^{[1
]}

Ohkuma, Takeshi ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 09期

基金：

日本学术振兴会;

关键词：

Photochemistry; Furan; Alkene; Cycloaddition; Diels-Alder reaction; DIELS-ALDER REACTIONS; ORGANIC-SYNTHESIS; CATION; CYCLOADDITION; 1,3-CYCLOHEXADIENE; 1,3-DIENES; DIENE; ACID; KETONES;

D O I：

10.1016/j.tetlet.2009.12.123

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photosensitized reaction of furan with a non-activated simple alkene was investigated Intramolecular Diels-Alder-type cycloaddition reactions between furan and a trisubstituted alkene were found 10 proceed in high yield in the presence of 9,10-dicyanoanthracene under UV irradiation to afford oxabicyclo[2 2 1]heptane derivatives in high stereoselectivity when the furan was alkyl substituted. On the other hand, the aryl-substituted furan cyclized via a completely different pathway to give spirocyclic and tricyclic products. (C) 2009 Elsevier Ltd All rights reserved.

引用

页码：1273 / 1275

页数：3

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