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Tetrabutylammonium Cyanide Catalyzed Diastereoselective Cyanosilylation of Chiral α-Hydroxyketones.

✍ Scribed by Inigo Amurrio; Ruben Cordoba; Aurelio G. Csaky; Joaquin Plumet

Publisher
John Wiley and Sons
Year
2005
Weight
17 KB
Volume
36
Category
Article
ISSN
0931-7597

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a,b-Unsaturated imines, obtained from cis-17-silyloxy-16-amino steroids and a,b-unsaturated aldehydes, react with diazomethane in the presence of a catalytic amount of Pd(OAc) 2 with high chemo-and diastereoselectivities to form steroidal cyclopropanocarbaldimines; chromatography on silica gel gives