Asymmetric Ozone Oxidation of Silylalkenes Using a C-2-Symmetrical Dialkoxysilyl Group as a Chiral Auxiliary

作者：Igawa Kazunobu; Kawasaki Yuuya; Nishino Kosuke; Mitsuda Naoto; Tomooka Katsuhiko^*

来源：Chemistry - A European Journal, 2014, 20(30): 9255-9258.

DOI：10.1002/chem.201402996

• acyloin
• alkenes
• asymmetric oxidation
• ozone
• silylperoxide

Ozone oxidation of silyl-substituted alkenes, namely silylalkenes, proceeds in an addition-type manner to afford alpha-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.

• 出版日期2014-7-21