Related Experiment Video
Updated: Apr 28, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Asymmetric ozone oxidation of silylalkenes using a C2-symmetrical dialkoxysilyl group as a chiral auxiliary
Kazunobu Igawa1, Yuuya Kawasaki, Kosuke Nishino
1Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Fukuoka 816-8580 (Japan), Fax: (+81) 92-583-7810.
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.
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Radical Anti-Markovnikov Addition to Alkenes: Overview
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Preparation and Reactions of Sulfides

