Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate

被引:85
作者
Trost, BM [1 ]
Aponick, A [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/ja0578348
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The palladium-catalyzed asymmetric allylic alkylation of a 1:1 mixture of DL- and meso-1,2-divinylethylene carbonate is reported. For the first time, both the ionization and nucleophilic addition steps of the catalytic cycle act as enantiodiscriminating steps to give a single product in high enantiomeric excess. The reactions proceed in >98% ee to efficiently generate useful chiral building blocks from acrolein. The absolute and relative configurations of iso-cladospolide B and 11-epi-iso-cladospolide B were verified by total synthesis, solving an apparent discrepancy in the literature. Copyright © 2006 American Chemical Society.
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页码:3931 / 3933
页数:3
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