Asymmetric Ozone Oxidation of Silylalkenes Using a C₂‐Symmetrical Dialkoxysilyl Group as a Chiral Auxiliary

Abstract

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.

Ozone Oxidation of Silylalkene: Mechanistic Study and Application for the Synthesis of Silacarboxylic Acid Derivatives

“…In 2006, we explored this reaction during our study on silylalkenes, finding that the ozone oxidation of alkenes 1 with sterically hindered silyl groups, such as SiEt 3 , Si i -Pr 3 , and Si t -BuPh 2 , provides easily isolable α-silylperoxy carbonyl compounds 2 (Scheme ). − …”