Synthesis of enantiomerically pure ( R)- and ( S)-2-ethoxycarbonylmethyl-2-hydroxy-cyclohexanones

Synthesis of enantiomerically pure ( R)- and ( S)-2-ethoxycarbonylmethyl-2-hydroxy-cyclohexanones

Sulfenylation of 2-p-tolylsulfinyl cyclohexanone can be achieved at −78°C with thiosulfonates. The in situ aldol reaction of these compounds with ethyl acetate enolate is highly stereoselective (1,2-asymmetric induction) and yields diastereomeric mixtures of β-hydroxyesters (the configuration of the...

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Bibliographic Details
Published in:Tetrahedron: asymmetry Vol. 9; no. 19; pp. 3445 - 3453
Main Authors: Garcı́a Ruano, José L, Barros, David, Maestro, M.Carmen, Alcudia, Ana, Fernández, Inmaculada
Format: Journal Article
Language:English
Published: Elsevier Ltd 02-10-1998
Online Access:Get full text
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Summary:Sulfenylation of 2-p-tolylsulfinyl cyclohexanone can be achieved at −78°C with thiosulfonates. The in situ aldol reaction of these compounds with ethyl acetate enolate is highly stereoselective (1,2-asymmetric induction) and yields diastereomeric mixtures of β-hydroxyesters (the configuration of the major one being dependent on the sulfenylating agent) that can be readily separated and transformed into the enantiomerically pure title ketones.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(98)00367-X