Enantioselective synthesis of (R)-(-)-baclofen via Ru(II)-BINAP catalyzed asymmetric hydrogenation
A short and efficient enantioselective synthesis of (R)-(-)-baclofen, a selective GABAB agonist has been described with an overall yield of 26% and 90% ee. Ru(II)-(S)-BINAP catalyzed asymmetric hydrogenations of C=C and C=O groups constitute the key steps in introducing stereogenic centers into the molecule.
A chemoenzymatic strategy for the synthesis of enantiopure (R)-(-)-baclofen
A seven-step enantioselective synthesis of (R)-(-)-baclofen 1 is described. The strategy developed involved as a key step, a microbiologically mediated Baeyer Villiger oxidation of the prochiral 3-(4'-chlorobenzyl)-cyclobutanone 3 which led to the optically pure (R)-(-)-4 lactone. This was further transformed throughout chemospecific reactions into the target molecule (R)-(-)-1.
Mazzini, Claudio,Lebreton, Jacques,Alphand, Veronique,Furstoss, Roland
p. 1195 - 1196
(2007/10/03)
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