Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations

Shan Wang, Jian-Xin Zhang, Tian-Yi Zhang, Huan Meng, Bi-Hong Chen and Wei Shu ()
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Shan Wang: Southern University of Science and Technology
Jian-Xin Zhang: Southern University of Science and Technology
Tian-Yi Zhang: Southern University of Science and Technology
Huan Meng: Southern University of Science and Technology
Bi-Hong Chen: Southern University of Science and Technology
Wei Shu: Southern University of Science and Technology

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Chiral aliphatic amine and alcohol derivatives are ubiquitous in pharmaceuticals, pesticides, natural products and fine chemicals, yet difficult to access due to the challenge to differentiate between the spatially and electronically similar alkyl groups. Herein, we report a nickel-catalyzed enantioselective hydroalkylation of acyl enamines and enol esters with alkyl halides to afford enantioenriched α-branched aliphatic acyl amines and esters in good yields with excellent levels of enantioselectivity. The operationally simple protocol provides a straightforward access to chiral secondary alkyl-substituted amine and secondary alkyl-substituted alcohol derivatives from simple starting materials with great functional group tolerance.

Date: 2021
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DOI: 10.1038/s41467-021-22983-7

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