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A polymer-enlarged homogeneously soluble oxazaborolidine catalyst for the asymmetric reduction of ketones by borane

✍ Scribed by Marcel Felder; Guido Giffels; Christian Wandrey

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 191 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(97)00192-4

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✦ Synopsis

A polymer-enlarged homogeneously soluble oxazaborolidine catalyst has been prepared and used in the enantioselective borane reduction of ketones. The catalyst is derived from (2S,4R)-ot,ot-diphenyl-2-[(4-allyloxy)-N-benzyloxycarbonyl]pyrrolidinemethanol 3 and a methyl hydrosiloxane---dimethylsiloxane copolymer 4 (15% functionalized). Enantioselective reduction of prochiral ketones to the corresponding chiral alcohols proceeds with enantiomeric excesses up to 98%. The catalyst can be retained by a nanofiltration membrane and thus could be recovered after reaction or used in a continuously operated membrane reactor. (~) 1997 Elsevier Science Ltd

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