Pyrinap ligands for enantioselective syntheses of amines

Qi Liu, Haibo Xu, Yuling Li, Yuan Yao, Xue Zhang, Yinlong Guo and Shengming Ma ()
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Qi Liu: Chinese Academy of Sciences
Haibo Xu: Chinese Academy of Sciences
Yuling Li: Chinese Academy of Sciences
Yuan Yao: Fudan University
Xue Zhang: Chinese Academy of Sciences
Yinlong Guo: Chinese Academy of Sciences
Shengming Ma: Chinese Academy of Sciences

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: Abstract Amines are a class of compounds of essential importance in organic synthesis, pharmaceuticals and agrochemicals. Due to the importance of chirality in many practical applications of amines, enantioselective syntheses of amines are of high current interest. Here, we wish to report the development of (R,Ra)-N-Nap-Pyrinap and (R,Sa)-N-Nap-Pyrinap ligands working with CuBr to catalyze the enantioselective A3-coupling of terminal alkynes, aldehydes, and amines affording optically active propargylic amines, which are platform molecules for the effective derivatization to different chiral amines. With a catalyst loading as low as 0.1 mol% even in gram scale reactions, this protocol is applied to the late stage modification of some drug molecules with highly sensitive functionalities and the asymmetric synthesis of the tubulin polymerization inhibitor (S)-(-)-N-acetylcolchinol in four steps. Mechanistic studies reveal that, unlike reported catalysts, a monomeric copper(I) complex bearing a single chiral ligand is involved in the enantioselectivity-determining step.

Date: 2021
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DOI: 10.1038/s41467-020-20205-0

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