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Molecules 2010, 15(4), 2453-2472; doi:10.3390/molecules15042453
Article

Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst

1
,
1, 2, 2 and 1,*
1 Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK 2 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 / Revised: 29 March 2010 / Accepted: 2 April 2010 / Published: 8 April 2010
(This article belongs to the Special Issue Bifunctional Catalysis)
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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 reductive amination; asymmetric hydrogenation; bifunctional catalyst; aliphatic ketones; chiral amines
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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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.

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