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

Research output: Contribution to journalArticle

32 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 languageEnglish
Pages (from-to)9816-9818
Number of pages3
JournalJournal of Organic Chemistry
Volume68
Issue number25
DOIs
Publication statusPublished - 2003 Dec 12

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Camphor
Stereoselectivity
Epoxidation
Anhydrides
Epoxy Compounds
Isomers
Hydrogen Peroxide
Urea
Acids
methyl(trifluoromethyl)dioxirane
carbamide peroxide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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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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T1 - Epoxidation of Chiral Camphor N-Enoylpyrazolidinones with Methyl(trifluoromethyl)dioxirane and Urea Hydrogen Peroxide/Acid Anhydride

T2 - Reversal of Stereoselectivity

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

N2 - 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.

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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