Collective synthesis of acetylenic pharmaceuticals via enantioselective Nickel/Lewis acid-catalyzed propargylic alkylation

Xihao Chang, Jiayin Zhang, Lingzi Peng and Chang Guo ()
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Xihao Chang: University of Science and Technology of China
Jiayin Zhang: University of Science and Technology of China
Lingzi Peng: University of Science and Technology of China
Chang Guo: University of Science and Technology of China

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

Abstract: Abstract Chiral acetylenic derivatives are found in many bioactive compounds and are versatile functional groups in organic chemistry. Here, we describe an enantioselective nickel/Lewis acid-catalyzed asymmetric propargylic substitution reaction from simple achiral materials under mild condition. The introduction of a Lewis acid cocatalyst is crucial to the efficiency of the transformation. Notably, we investigate this asymmetric propargylic substitution reaction for the development of a range of structurally diverse natural products. The power of this strategy is highlighted by the collective synthesis of seven biologically active compounds: (−)-Thiohexital, (+)-Thiopental, (+)-Pentobarbital, (−)-AMG 837, (+)-Phenoxanol, (+)-Citralis, and (−)-Citralis Nitrile.

Date: 2021
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DOI: 10.1038/s41467-020-20644-9

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