Synthesis of (alpha R,beta S)-epoxyketones by asymmetric epoxidation of chalcones with cinchona phase-transfer catalysts

Title
Synthesis of (alpha R,beta S)-epoxyketones by asymmetric epoxidation of chalcones with cinchona phase-transfer catalysts
Author(s)
유미숙[유미숙]김동국하민우[하민우]주상섭[주상섭]박형근[박형근]정병선
Keywords
HIGHLY ENANTIOSELECTIVE EPOXIDATION; TRANSFER MEDIATED EPOXIDATION; ELECTRON-DEFICIENT OLEFINS; ALPHA,BETA-UNSATURATED KETONES; ALDOL REACTIONS; AMMONIUM-SALTS; CROWN-ETHERS; D-GLUCOSE; TRICHLOROISOCYANURIC ACID; GLYCOLATE ALKYLATION
Issue Date
201010
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Citation
TETRAHEDRON LETTERS, v.51, no.42, pp.5601 - 5603
Abstract
An efficient method to synthetically produce optically enriched (alpha R,beta S)-epoxyketones was developed using a quaternary ammonium salt derived from cinchona alkaloid as the chiral phase-transfer catalyst. (alpha R,beta S)-Epoxyketones were prepared in high optical purities (91-99% ee) by the asymmetric epoxidation of 1,3-diarylenones with aqueous sodium hypochlorite in the presence of a hydrocinchonine-derived chiral phase-transfer catalyst bearing a 2,3,4-trifluorobenzyl group. (C) 2010 Elsevier Ltd. All rights reserved.
URI
http://hdl.handle.net/YU.REPOSITORY/23477http://dx.doi.org/10.1016/j.tetlet.2010.08.056
ISSN
0040-4039
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약학대학 > 약학부 > Articles
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