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

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.

SUBMITTER: Wang S

PROVIDER: S-EPMC8119980 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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

Wang Shan S Zhang Jian-Xin JX Zhang Tian-Yi TY Meng Huan H Chen Bi-Hong BH Shu Wei W

Nature communications 20210513 1

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 enantioselec ...[more]

PMID: 33986269

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