Diastereoselectivity in the reduction of alpha-Oxy- and alpha-amino-substituted acyclic ketones by polymethylhydrosiloxane.
Diastereoselectivity in the reduction of alpha-alkoxy-, alpha-acyloxy-, and alpha-alkylamino-substituted ketones with polymethylhydrosiloxane (PMHS) in the presence of fluoride ion catalysis was investigated. High syn-selectivity was observed in the reduction of alpha-alkoxy, alpha-acyloxy, and alpha-dialkylamino ketones. Reduction of alpha-monoalkylamino ketone proceeded in anti-selective manner with moderate selectivity. The observed selectivity is explained based on Felkin-Anh and Cram-chelate models.
Nadkarni
Durgesh
D
Process Development Laboratories, Pfizer Global Manufacturing, Eastern Point Road, Groton, Connecticut 06340, USA. durgesh.nadkarni@pfizer.com
Hallissey
James
J
Mojica
Carlos
C