Diastereoselective photosensitised radical addition to fumaric acid derivatives bearing oxazolidine chiral auxiliaries

被引:27
作者
Campari, G [1 ]
Fagnoni, M [1 ]
Mella, M [1 ]
Albini, A [1 ]
机构
[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
关键词
D O I
10.1016/S0957-4166(00)00138-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Various fumaric acid diamides were alkylated by reaction with photogenerated radicals. The radicals were produced either by benzophenone triplet hydrogen abstraction (from 1,3-dioxolane, 2-methyl-1,3-dioxolane and adamantane) or via photoinduced electron transfer sensitised by DCN/biphenyl from stannanes (t-BuSnPh3 and Bu4Sn). When chiral substrates were employed the reaction occurred with a good degree of stereoselectivity even when acyclic alkyl radicals were involved. (C) 2000 Elsevier Science Ltd. All rights reserved.
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页码:1891 / 1906
页数:16
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