Evolution of titanium(IV) alkoxides and raney nickel for asymmetric reductive amination of prochiral aliphatic ketones

Thomas C Nugent; Vijay N Wakchaure; Abhijit K Ghosh; Rashmi R Mohanty

doi:10.1021/ol051909v

Evolution of titanium(IV) alkoxides and raney nickel for asymmetric reductive amination of prochiral aliphatic ketones

Org Lett. 2005 Oct 27;7(22):4967-70. doi: 10.1021/ol051909v.

Authors

Thomas C Nugent¹, Vijay N Wakchaure, Abhijit K Ghosh, Rashmi R Mohanty

Affiliation

¹ Department of Chemistry, School of Engineering and Science, International University Bremen, Germany. t.nugent@iu-bremen.de

PMID: 16235934
DOI: 10.1021/ol051909v

Abstract

[reaction: see text] A new method for the one-pot asymmetric reductive amination of prochiral aliphatic ketones has been developed. The previously unexplored reagent combination of Ti(O(i)Pr)(4)/Raney Ni/H(2) in the presence of (R)- or (S)-alpha-methylbenzylamine provides good to excellent yield (76-90%) and diastereomeric excess (72-98%). The second step, hydrogenolysis, provides the corresponding primary amine in high yield (88-93%) and with uncompromised enantiomeric excess.