Substrate modification as a means of enhancing the enantioselectivity of microbial reductions of β-keto esters. An (R)- or (S )-1,3,5-trihydroxypentane synthon
The enantioselectivity of yeast-mediated reduction of 5-(benzyloxy)-3-oxopentanoate esters can be optimized by simple selection of a suitable ester alkoxy group. The resulting chiral 5-(benzyloxy)-3-hydroxypentanoates with > 95% ee can serve as either an (R)- or (S)-1,3,5-trihydroxypentane synthon for asymmetric syntheses. The synthesis of a key optically active intermediate for (S)-(-)-lipoic acid is provided as an example.
Brooks, Dee W.,Kellogg, Rosemary P.,Cooper, Curt S.
p. 192 - 196
(2007/10/02)
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