Synthesis of Ro 25-8210 via an enantioselective oxazaborolidine-catalyzed reduction

KG Hull, M Visnick, W Tautz, A Sheffron

Index: Hull, Kenneth G.; Visnick, Mike; Tautz, William; Sheffron, Allen Tetrahedron, 1997 , vol. 53, # 37 p. 12405 - 12414

Full Text: HTML

Citation Number: 21

Abstract

Prochiral ketones which contain nitrogen atoms have been reduced enantioselectively with chiral oxazaborolidines in the presence of excess borane. However, the pyridine system has been shown to be a poor substrate for this asymmetric reduction. For example, catalytic reduction of 2-acetylpyridine with a chiral oxazaborolidine provided the product alcohol in only 28% ee. We wish to report the enantioselective reduction of 2-(bromoacetyl)-pyridine ...