Asymmetric Ozone Oxidation of Silylalkenes Using a C-2-Symmetrical Dialkoxysilyl Group as a Chiral Auxiliary
Asymmetric Ozone Oxidation of Silylalkenes Using a C-2-Symmetrical Dialkoxysilyl Group as a Chiral Auxiliary
复制标题
使用 C-2-对称二烷氧基甲硅烷基作为手性助剂对甲硅烷基烯烃进行不对称臭氧氧化
DOI：
10.1002/chem.201402996
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发表时间：
2014
影响因子：
4.3
通讯作者：
K. Tomooka
中科院分区：
文献类型：
--
作者：
K. Igawa;Y. Kawasaki;K. Nishino;N. Mitsuda;K. Tomooka
甲硅烷基取代的烯烃（即甲硅烷基烯烃）的臭氧氧化以加成型方式进行，以良好至优异的产率得到α-甲硅烷基过氧羰基化合物，而不形成正常的臭氧分解产物。本文报道了由炔和新设计的手性氢硅烷制备的手性烯基硅烷的臭氧氧化。该反应提供具有高非对映选择性（高达94 % d.r.）的甲硅烷基过氧化物。甲硅烷基过氧化物可以立体特异性方式转化为对映体富集的手性偶姻。
Ozone oxidation of silyl‐substituted alkenes, namely silylalkenes, proceeds in an addition‐type manner to afford α‐silylperoxy carbonyl compounds in good to excellent yields, without the formation of normal ozonolysis products. Herein the ozone oxidation of chiral alkenylsilanes prepared from alkynes and a newly designed chiral hydrosilane is reported. The reaction affords silylperoxides with high diastereoselectivity (up to 94 % d.r.). The silylperoxides are convertible into enantioenriched chiral acyloins in a stereospecific manner.