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羰基-烯烃光环加成反应的自旋导向立体选择性

Spin-directed stereoselectivity of carbonyl-alkene photocycloadditions.

作者信息

Griesbeck AG, Fiege M, Bondock S, Gudipati MS

机构信息

Institute of Organic Chemistry, Greinstrasse 4, and Institute of Physical Chemistry, Luxemburger Strasse 116, University of Cologne, D-50939 Koln, Germany.

出版信息

Org Lett. 2000 Nov 16;2(23):3623-5. doi: 10.1021/ol006502z.

Abstract

The concentration dependence of the Paterno-Buchi photocycloaddition of the two cyclic enolethers 2,3-dihydrofuran and 2,3-dihydropyran, respectively, with aromatic as well as aliphatic aldehydes was studied. For aliphatic aldehydes, a sharp transition from low to high diastereostereoselectivity was observed, indicating a switch from singlet to triplet photocycloaddition with different selectivity controlling mechanisms.

摘要

分别研究了两种环状烯醚2,3-二氢呋喃和2,3-二氢吡喃与芳香醛以及脂肪醛的帕特诺-布齐光环加成反应的浓度依赖性。对于脂肪醛,观察到从低非对映选择性到高非对映选择性的急剧转变,这表明从单线态到三线态光环加成反应发生了转变,且具有不同的选择性控制机制。

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