Stereoselective pinacol-type rearrangement of 2,3-epoxy alcohols with retention of configuration mediated by bis(iodozincio)methane

被引：0
|
作者：
Matsubara, S [1 ]
Yamamoto, H [1 ]
Oshima, K [1 ]
机构：
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2002年 / 41卷 / 15期
关键词：
asymmetric synthesis; Lewis acids; nucleophiles; rearrangement; zinc;
D O I：
10.1002/1521-3773(20020802)41:15<2837::AID-ANIE2837>3.0.CO;2-X
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Retention of the configuration is observed in the pinacol-type rearrangement of 2,3-epoxy alcohols 1 in the presence of bis(iodozincio)methane (2). The 1,3-migration of the hydroxymethyl group affords an intermediate 2-hydroxyaldehyde, which is methylenated by 2 in situ to give homoallyl alcohol 3.
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页码：2837 / +
页数：5
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