title: 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.
authors.affiliation: Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Fukuoka 816-8580 (Japan), Fax: (+81) 92-583-7810.
authors.forename: Kazunobu
authors.initials: K
authors.lastname: Igawa
authors.forename: Yuuya
authors.initials: Y
authors.lastname: Kawasaki
authors.forename: Kosuke
authors.initials: K
authors.lastname: Nishino
authors.forename: Naoto
authors.initials: N
authors.lastname: Mitsuda
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Tomooka
keywords: acyloin; alkenes; asymmetric oxidation; ozone; silylperoxide