Evolution of titanium(IV) alkoxides and raney nickel for asymmetric reductive amination of prochiral aliphatic ketones.
[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.
Nugent
Thomas C
TC
Department of Chemistry, School of Engineering and Science, International University Bremen, Germany. t.nugent@iu-bremen.de
Wakchaure
Vijay N
VN
Ghosh
Abhijit K
AK
Mohanty
Rashmi R
RR