Indolinylmethanol catalyzed enantioselective Reformatsky reaction with ketones

A series of chiral indolinylmethanol ligands have been applied for the first time in the asymmetric Reformatsky reaction of an alpha-bromoester with ketones. In the presence of NiBr2 and zinc powder, up to 75% yield and 87% ee were obtained for a variety of aromatic and aliphatic ketones. The use of Ni(acac)(2) resulted in 96% ee although the corresponding yield was low. This process provided a convenient method to access synthetically useful chiral beta-hydroxyesters. (C) 2010 Elsevier Ltd. All rights reserved.