"Asymmetric Hydrogenation of Furan-containing Kethoesters over Tartaric Acid-Modified Raney Nickel Catalyst".

NORIKO HARUNA; DELICIA ACOSTA; NAKAGAWA SATOSHI; KOHEI YAMAGUCHI; AKIRA TAI; TAKASHI SUGUIMURA

Heterocycle

Harima Himeji Institute of Technology

Lugar: Himeji; Año: 2004 vol. 62 p. 375 - 386

Abstract ?The hydrogenation of β-ketoesters containing a furan unit at the conjugated position to the ketone was carried out over a chiral heterogeneous catalyst, tartaric acid-modified Raney nickel. The hydrogenation first proceeds at the ketone part of the substrate to give optically active alcohols, but a simple substrate undergoes further hydrogenation of the furan part to produce a diastereomeric mixture of alcohols having a tetrahydrofuran moiety. This overreduction was efficiently suppressed by substitutions of a substituent at the furan part. The optical yield of the product at the hydroxy group is in the range of 40?90%.