Chiral aldehyde-nickel dual catalysis enables asymmetric α−propargylation of amino acids and stereodivergent synthesis of NP25302

Fang Zhu, Chao-Xing Li, Zhu-Lian Wu, Tian Cai, Wei Wen () and Qi-Xiang Guo ()
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Fang Zhu: Southwest University
Chao-Xing Li: Southwest University
Zhu-Lian Wu: Southwest University
Tian Cai: Southwest University
Wei Wen: Southwest University
Qi-Xiang Guo: Southwest University

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

Abstract: Abstract The combined catalytic systems derived from organocatalysts and transition metals exhibit powerful activation and stereoselective-control abilities in asymmetric catalysis. This work describes a highly efficient chiral aldehyde-nickel dual catalytic system and its application for the direct asymmetric α−propargylation reaction of amino acid esters with propargylic alcohol derivatives. Various structural diversity α,α−disubstituted non-proteinogenic α−amino acid esters are produced in good-to-excellent yields and enantioselectivities. Furthermore, a stereodivergent synthesis of natural product NP25302 is achieved, and a reasonable reaction mechanism is proposed to illustrate the observed stereoselectivity based on the results of control experiments, nonlinear effect investigation, and HRMS detection.

Date: 2022
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DOI: 10.1038/s41467-022-35062-2

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