HOMOGENEOUS AND HETEROGENEOUS ASYMMETRIC REACTIONS - PART IX - ASYMMETRIC TRANSFER HYDROGENATION OF 16-METHYL-SUBSTITUTED STEROID 17-KETONES IN THE PRESENCE OF RHODIUM(I) COMPLEXES
B. Torok et al., HOMOGENEOUS AND HETEROGENEOUS ASYMMETRIC REACTIONS - PART IX - ASYMMETRIC TRANSFER HYDROGENATION OF 16-METHYL-SUBSTITUTED STEROID 17-KETONES IN THE PRESENCE OF RHODIUM(I) COMPLEXES, Reaction kinetics and catalysis letters, 64(1), 1998, pp. 35-40
Chiral transfer hydrogenation of 16 methyl-substituted steroid 17-keto
nes in the presence of rhodium(I) complexes by hydrosilylation is desc
ribed. During the preparation of the complex catalysts a wide variety
of bidentate phosphines were used including chiral ligands, as well. T
he diastereoselectivity of the reduction depends strongly on the struc
ture of the ligands. The method applied produces the hydroxy steroid p
roducts with excellent yield under very mild reaction conditions. Addi
tionally, the procedure makes possible the preparation of 17 alpha-OH
isomers beside the easily synthesizable 17 beta-OH products.