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Show simple item record Meth-Cohn, O Horak, RM Fouché, Gerda 2007-06-29T09:37:36Z 2007-06-29T09:37:36Z 1994-06-07
dc.identifier.citation Meth-Cohn, O, Horak, RM and Fouche, G. 1994. Bakers yeast-mediated transformations of alpha-keto epoxides. Journal of the Chemical Society-Perkin Transactions 1, pp 1517-1527 en
dc.identifier.issn 0300-922X
dc.description Copyright: 1994 Royal Society Chemistry en
dc.description.abstract Alpha beta-Epoxy ketones on treatment with baker's yeast yield different types of products depending on their substitution. Small groups such as H or Me attached at the epoxy end protect that end from attack. Thus, 1-acyl epoxides with H, methyl or propyl as the 2-epoxy substituent give solely the epoxy alcohol product with moderate stereoselectivity (13-64% d.e.). With a 2-phenyl substituent the sole product is the 1.2.3-triol as a single racemic diastereoisomer derived by a reduction/hydrolysis sequence involving a syn ring-opening of the epoxide. More than one enzyme is probably involved in both of these transformations which tend to favour S-reduction. The detailed mechanism of product formation in both processes has been undertaken and the formation of the triols has been shown by O-18 labelling studies to involve asymmetric reduction of the ketone and a double inversion during epoxide ring-opening involving a carbocation intermediate. en
dc.language.iso en en
dc.publisher Royal Society Chemistry en
dc.subject Baker's yeast en
dc.subject Stereoselectivity en
dc.subject Epoxides en
dc.subject Alpha beta-Epoxy ketones en
dc.subject Organic chemistry en
dc.title Bakers yeast-mediated transformations of alpha-keto epoxides en
dc.type Article en

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