Enantioselective hydrogenation of N-H imines.
N-H ketoimines 3a-3v are readily prepared in high yield via organometallic addition to nitriles and isolated as corresponding bench-stable hydrochloride salts. Homogeneous asymmetric hydrogenation of unprotected N-H ketoimines 3a-3v using Ir-(S,S)-f-binaphane as catalyst provides chiral amines 4a-4v in 90-95% yield with enantioselectivities up to 95% ee.
Hou
Guohua
G
Department of Chemistry, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854-8066, USA.
Gosselin
Francis
F
Li
Wei
W
McWilliams
J Christopher
JC
Sun
Yongkui
Y
Weisel
Mark
M
O'Shea
Paul D
PD
Chen
Cheng-yi
CY
Davies
Ian W
IW
Zhang
Xumu
X
D006865:Hydrogenation; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007097:Imines