Iridium-catalyzed direct asymmetric reductive amination utilizing primary alkyl amines as the N-sources

Zitong Wu, Wenji Wang, Haodong Guo, Guorui Gao, Haizhou Huang and Mingxin Chang ()
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Zitong Wu: Northwest A&F University
Wenji Wang: Northwest A&F University
Haodong Guo: Northwest A&F University
Guorui Gao: Shandong Normal University
Haizhou Huang: Northwest A&F University
Mingxin Chang: Northwest A&F University

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract Direct asymmetric reductive amination is one of the most efficient methods for the construction of chiral amines, in which the scope of the applicable amine coupling partners remains a significant challenge. In this study we describe primary alkyl amines effectively serve as the N-sources in direct asymmetric reductive amination catalyzed by the iridium precursor and sterically tunable chiral phosphoramidite ligands. The density functional theory studies of the reaction mechanism imply the alkyl amine substrates serve as a ligand of iridium strengthened by a (N)H-O(P) hydrogen-bonding attraction, and the hydride addition occurs via an outer-sphere transition state, in which the Cl-H H-bonding plays an important role. Through this concise procedure, cinacalcet, tecalcet, fendiline and many other related chiral amines have been synthesized in one single step with high yields and excellent enantioselectivity.

Date: 2022
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DOI: 10.1038/s41467-022-31045-5

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