Catalytic asymmetric epoxidation of α, β-unsaturated carbonyl compounds

Tetsuhiro Nemoto, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journalReview article

70 Citations (Scopus)

Abstract

This article summarizes recent progress in catalytic asymmetric epoxidation of α, β-unsaturated carbonyl compounds. Asymmetric epoxidation of α, β-unsaturated carbonyl compounds remains one of the most important functional group manipulations in organic synthesis, because of the usefulness of the corresponding enantiomerically enriched α, β-epoxy carbonyl compounds. Since the initial repog by Juliá and co-workers, catalytic asymmetric epoxidation of α, β-epoxy ketones (enones) has been studied using several methodologies. In recent years, we and others have achieved efficient catalytic asymmetric epoxidation of enones using a variety of catalysts, including phase-transfer catalysts, polyamino acid catalysts, chiral ligand-metal peroxide complexes, and so on. On the other hand, there are only a few reports of catalytic asymmetric epoxidation of α, β-unsaturated carboxylic acid derivatives. Very recently we have reported the first example of a general catalytic asymmetric epoxidation of α,β-unsaturated carboxylic acid imidazolides to afford the corresponding α, β-epoxy peroxycarboxylic acid tert-butyl esters, which are transformed efficiently into α, β-epoxy esters, amides, aldehydes, and γ, δ-epoxy β-keto esters. The mechanism of the several reactions and applications to a catalytic asymmetric synthesis of biologically active compounds are also described briefly.

Original languageEnglish
Pages (from-to)94-105
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume60
Issue number2
DOIs
Publication statusPublished - Jan 1 2002
Externally publishedYes

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Carbonyl compounds
Epoxidation
Esters
Carboxylic Acids
Ketones
Catalysts
Acids
Peroxides
Aldehydes
Amides
Functional groups
Metals
Ligands
Derivatives

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Catalytic asymmetric epoxidation of α, β-unsaturated carbonyl compounds. / Nemoto, Tetsuhiro; Ohshima, Takashi; Shibasaki, Masakatsu.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 60, No. 2, 01.01.2002, p. 94-105.

Research output: Contribution to journalReview article

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