Asymmetric ozone oxidation of silylalkenes using a C2- symmetrical dialkoxysilyl group as a chiral auxiliary

Kazunobu Igawa, Yuuya Kawasaki, Kosuke Nishino, Naoto Mitsuda, Katsuhiko Tomooka

Research output: Contribution to journalArticle

3 Citations (Scopus)

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. Putting ozone to work: Ozone oxidation of chiral alkenylsilanes prepared from alkynes and a newly designed chiral hydrosilane affords silylperoxides with high diastereoselectivity (up to 94 % d.r.; see scheme). The silylperoxides are convertible into enantioenriched chiral acyloins in a stereospecific manner.

Original languageEnglish
Pages (from-to)9255-9258
Number of pages4
JournalChemistry - A European Journal
Volume20
Issue number30
DOIs
Publication statusPublished - Jul 21 2014

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Ozone
Oxidation
Alkynes
Carbonyl compounds
Alkenes
Olefins
acyloin

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Asymmetric ozone oxidation of silylalkenes using a C2- symmetrical dialkoxysilyl group as a chiral auxiliary. / Igawa, Kazunobu; Kawasaki, Yuuya; Nishino, Kosuke; Mitsuda, Naoto; Tomooka, Katsuhiko.

In: Chemistry - A European Journal, Vol. 20, No. 30, 21.07.2014, p. 9255-9258.

Research output: Contribution to journalArticle

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AU - Tomooka, Katsuhiko

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AB - 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. Putting ozone to work: Ozone oxidation of chiral alkenylsilanes prepared from alkynes and a newly designed chiral hydrosilane affords silylperoxides with high diastereoselectivity (up to 94 % d.r.; see scheme). The silylperoxides are convertible into enantioenriched chiral acyloins in a stereospecific manner.

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