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Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst†
Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK
AstraZeneca, Silk Road Business Park, Macclesfield, SK10 2NA, UK
† Dedicated to the memory of Professor José M. Concellón.
* Author to whom correspondence should be addressed.
Received: 9 March 2010; in revised form: 29 March 2010 / Accepted: 2 April 2010 / Published: 8 April 2010
Abstract: 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.
Keywords: reductive amination; asymmetric hydrogenation; bifunctional catalyst; aliphatic ketones; chiral amines
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Villa-Marcos, B.; Li, C.; Mulholland, K.R.; Hogan, P.J.; Xiao, J. Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst. Molecules 2010, 15, 2453-2472.
Villa-Marcos B, Li C, Mulholland KR, Hogan PJ, Xiao J. Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst. Molecules. 2010; 15(4):2453-2472.
Villa-Marcos, Barbara; Li, Chaoqun; Mulholland, Keith R.; Hogan, Philip J.; Xiao, Jianliang. 2010. "Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst." Molecules 15, no. 4: 2453-2472.