Exploiting Planar Chirality for the Generation of (alpha)-Ferrocenyl Stereogenic Centres

Addition of Grignard reagents R1MgBr (R1 = Me, Et, i-Pr, t-Bu, Ph) to 2-bromo- and 2trimethylsilylferrocenecarboxaldehyde proceeded, in most cases, with high diastereoselectivity to generate (alpha)-ferrocenyl alcohols of S*,pS* configuration. Following conversion into their corresponding acetates, reaction with dimethylamine provided (alpha)-ferrocenyl amines with retention of configuration (R1 = Me, Et, Ph).