Synlett 2006(3): 0403-0406  
DOI: 10.1055/s-2006-926258
LETTER
© Georg Thieme Verlag Stuttgart · New York

Enantioconvergent Access to the Enantiomerically Pure Building Blocks (+)- or (-)-4-Hydroxy-3-methyl-2-cyclohexenone Using a Chemoenzymatic Process

Elie Palombo, Gérard Audran*, Honoré Monti*
Laboratoire de Réactivité Organique Sélective, U.M.R. 6180 ‘Chirotechnologies: catalyse et biocatalyse’, Université Paul Cézanne, Aix-Marseille III, 13397 Marseille Cedex 20, France
Fax: +33(4)91288862; e-Mail: g.audran@univ.u-3mrs.fr; e-Mail: honore.monti@univ.u-3mrs.fr;
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Publikationsverlauf

Received 7 December 2005
Publikationsdatum:
06. Februar 2006 (online)

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Abstract

A convenient chemoenzymatic enantioconvergent access to enantiomerically pure (+)- or (-)-4-hydroxy-3-methyl-2-cyclohexenone is described using a one-pot two-step kinetic resolution-stereoinversion protocol followed by hydrolysis. The key step of the sequence is the spontaneous elimination of an undesired stereocenter. The choice between enzymatic acyl transfer or ester alcoholysis of the corresponding racemic starting material, together with the selectivity of a lipase, determines the absolute configuration of the desired single enantiomer.