dc.contributor.author |
Meth-Cohn, O
|
|
dc.contributor.author |
Horak, RM
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|
dc.contributor.author |
Fouché, Gerda
|
|
dc.date.accessioned |
2007-06-29T09:37:36Z |
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dc.date.available |
2007-06-29T09:37:36Z |
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dc.date.issued |
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 |
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dc.identifier.uri |
http://hdl.handle.net/10204/815
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|
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 |
dc.identifier.apacitation |
Meth-Cohn, O., Horak, R., & Fouché, G. (1994). Bakers yeast-mediated transformations of alpha-keto epoxides. http://hdl.handle.net/10204/815 |
en_ZA |
dc.identifier.chicagocitation |
Meth-Cohn, O, RM Horak, and Gerda Fouché "Bakers yeast-mediated transformations of alpha-keto epoxides." (1994) http://hdl.handle.net/10204/815 |
en_ZA |
dc.identifier.vancouvercitation |
Meth-Cohn O, Horak R, Fouché G. Bakers yeast-mediated transformations of alpha-keto epoxides. 1994; http://hdl.handle.net/10204/815. |
en_ZA |
dc.identifier.ris |
TY - Article
AU - Meth-Cohn, O
AU - Horak, RM
AU - Fouché, Gerda
AB - 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.
DA - 1994-06-07
DB - ResearchSpace
DP - CSIR
KW - Baker's yeast
KW - Stereoselectivity
KW - Epoxides
KW - Alpha beta-Epoxy ketones
KW - Organic chemistry
LK - https://researchspace.csir.co.za
PY - 1994
SM - 0300-922X
T1 - Bakers yeast-mediated transformations of alpha-keto epoxides
TI - Bakers yeast-mediated transformations of alpha-keto epoxides
UR - http://hdl.handle.net/10204/815
ER -
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en_ZA |