Bifunctional catalysis: direct reductive amination of aliphatic ketones with an iridium-phosphate catalyst.
Chiral amines are one of the ubiquitous functional groups in fine chemical, pharmaceutical and agrochemical products, and the most convenient, economical, and eco-benign synthetic pathway to these amines is direct asymmetric reductive amination (DARA) of prochiral ketones. This paper shows that a wide range of aliphatic ketones can be directly aminated under hydrogenation conditions, affording chiral amines with good to excellent yields and with enantioselectivities up to 96% ee. The catalysis is effected by the cooperative action of a cationic Cp*Ir(III) complex and its phosphate counteranion.
Villa-Marcos
Barbara
B
Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool, UK. barvm@liv.ac.uk
Li
Chaoqun
C
Mulholland
Keith R
KR
Hogan
Philip J
PJ
Xiao
Jianliang
J
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*
D000588:Amines; D007659:Ketones; D010710:Phosphates; D007495:Iridium