Efficient approach to chiral ferrocenyl ligands via asymmetric hydrogenation of ferrocenyl ketone

ORGN 777

Albert S. C. Chan, bcachan@polyu.edu.hk, Wing Sze Lam, 03900892r@polyu.edu.hk, Stanton H. L. Kok, Fuk Loi Lam, Gamma H. Y. Cheung, Jing Wu, Terry T. L. Au-Yeung, and C. H. Yeung. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hung Hom, Hong Kong, China

 

Ferrrocene backbone catalyst has received much attention owing to its planar chirality possessing highly asymmetric induction ability.  However, its study is impeded by the tedious resolution of Ugi's amine.  CBS reduction shows a relatively short synthetic pathway to chiral ferrocenyl alcohol after Friedel-Crafts acylation but it requires up to 3 mol% of the expensive CBS catalyst. Asymmetric hydrogenation, on the other hand, is one of the best methods to generate a chiral alcohol in terms of its high S/C ratio, clean process and easy manipulation.  Recently, we have developed versatile P-Phos ligands and derivatives, and have shown them to be highly effective in the hydrogenation of various ferrocenyl ketone to the corresponding chiral ferrocenyl alcohols.