New and efficient chiral selenium electrophiles

被引：0
作者：
Uehlin, L
Fragale, G
Wirth, T [1 ]
机构：
[1] Univ Basel, Inst Organ Chem, CH-4056 Basel, Switzerland
[2] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2002年 / 8卷 / 05期
关键词：
alkenes; electrophiles; heterocycles; selenium; stereoselective synthesis;
D O I：
10.1002/1521-3765(20020301)8:5<1125::AID-CHEM1125>3.0.CO;2-I
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
New chiral diselenides were prepared in a few steps from readily available starting materials. The selenium electrophiles generated from these diselenides were used for the efficient stereoselective inter- and intramolecular functionalization of alkenes. The substitution pattern influences the stereoselectivities and protection of the hydroxy moiety in the chiral side chain led to increased selectivities and yields in the selenenylation reactions. An additional substituent in the second ortho position was advantageous as well. Addition products with up to 96% de were obtained. The influence of the nucleophile on the outcome of selenenylations of alkenes was studied to some extent as well.
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页码：1125 / 1133
页数：9
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