Organocatalytic kinetic resolution of a planar-chiral ferrocenecarbaldehyde

The proline-catalyzed aldol reaction of racemic 2-(2'-pyrimidyl)ferrocenecarbaldehyde with acetone in DMSO at room temperature constitutes as the first example of an organocatalytic kinetic resolution of a planar-chiral compound. The selectivity factor of the kinetic resolution is 9.2, and the stereochemical outcome of the process can be easily rationalized by the standard mechanistic model of the proline-catalyzed aldol reaction. (C) 2009 Elsevier Ltd. All rights reserved,