Epoxidation of Chiral Camphor N-Enoylpyrazolidinones with Methyl(trifluoromethyl)dioxirane and Urea Hydrogen Peroxide/Acid Anhydride: Reversal of Stereoselectivity

Chai Ling Fan; Wei Der Lee; Nai Wei Teng; Ying Chieh Sun; Kwunmin Chen

doi:10.1021/jo034807w

Epoxidation of Chiral Camphor N-Enoylpyrazolidinones with Methyl(trifluoromethyl)dioxirane and Urea Hydrogen Peroxide/Acid Anhydride: Reversal of Stereoselectivity

Chai Ling Fan, Wei Der Lee, Nai Wei Teng, Ying Chieh Sun, Kwunmin Chen

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

Both diastereomeric isomers of epoxides with high optical purity are obtained when camphor N-methacryl-oylpyrazolidinone (1a) and N-tigloylpyrazolidinone (1b) are treated with a urea hydrogen peroxide/TFAA and methyl-(trifluoromethyl)dioxirane, respectively.

Original language	English
Pages (from-to)	9816-9818
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	68
Issue number	25
DOIs	https://doi.org/10.1021/jo034807w
Publication status	Published - 2003 Dec 12

ASJC Scopus subject areas

Organic Chemistry

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Epoxidation of Chiral Camphor N-Enoylpyrazolidinones with Methyl(trifluoromethyl)dioxirane and Urea Hydrogen Peroxide/Acid Anhydride : Reversal of Stereoselectivity. / Fan, Chai Ling; Lee, Wei Der; Teng, Nai Wei; Sun, Ying Chieh ; Chen, Kwunmin.

In: Journal of Organic Chemistry, Vol. 68, No. 25, 12.12.2003, p. 9816-9818.

Research output: Contribution to journal › Article › peer-review

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abstract = "Both diastereomeric isomers of epoxides with high optical purity are obtained when camphor N-methacryl-oylpyrazolidinone (1a) and N-tigloylpyrazolidinone (1b) are treated with a urea hydrogen peroxide/TFAA and methyl-(trifluoromethyl)dioxirane, respectively.",

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AU - Fan, Chai Ling

AU - Lee, Wei Der

AU - Teng, Nai Wei

AU - Sun, Ying Chieh

AU - Chen, Kwunmin

PY - 2003/12/12

Y1 - 2003/12/12

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AB - Both diastereomeric isomers of epoxides with high optical purity are obtained when camphor N-methacryl-oylpyrazolidinone (1a) and N-tigloylpyrazolidinone (1b) are treated with a urea hydrogen peroxide/TFAA and methyl-(trifluoromethyl)dioxirane, respectively.

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Epoxidation of Chiral Camphor N-Enoylpyrazolidinones with Methyl(trifluoromethyl)dioxirane and Urea Hydrogen Peroxide/Acid Anhydride: Reversal of Stereoselectivity

Abstract

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