Journal of Organic Chemistry p. 192 - 196 (1987)
Update date:2022-07-29
Topics:
Brooks, Dee W.
Kellogg, Rosemary P.
Cooper, Curt S.
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.
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