Access to enantioenriched compounds bearing challenging tetrasubstituted stereocenters via kinetic resolution of auxiliary adjacent alcohols

Shengtong Niu, Hao Zhang, Weici Xu (), Prasanta Ray Bagdi, Guoxiang Zhang, Jinggong Liu, Shuang Yang and Xinqiang Fang ()
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Shengtong Niu: University of Chinese Academy of Sciences
Hao Zhang: University of Chinese Academy of Sciences
Weici Xu: University of Chinese Academy of Sciences
Prasanta Ray Bagdi: University of Chinese Academy of Sciences
Guoxiang Zhang: University of Chinese Academy of Sciences
Jinggong Liu: The Second Affiliated Hospital of Guangzhou University of Chinese Medicine
Shuang Yang: University of Chinese Academy of Sciences
Xinqiang Fang: University of Chinese Academy of Sciences

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

Abstract: Abstract Contemporary asymmetric catalysis faces huge challenges when prochiral substrates bear electronically and sterically unbiased substituents and when substrates show low reactivities. One of the inherent limitations of chiral catalysts and ligands is their incapability in recognizing prochiral substrates bearing similar groups. This has rendered many enantiopure substances bearing several similar substituents inaccessible. Here we report the rationale, scope, and applications of the strategy of kinetic resolution of auxiliary adjacent alcohols (KRA*) that can be used to solve the above troubles. Using this method, a large variety of optically enriched tertiary alcohols, epoxides, esters, ketones, hydroxy ketones, epoxy ketones, β-ketoesters, and tetrasubstituted methane analogs with two, three, and four spatially and electronically similar groups can be readily obtained (totally 96 examples). At the current stage, the strategy serves as the optimal solution that can complement the inability caused by direct asymmetric catalysis in getting chiral molecules with challenging fully substituted stereocenters.

Date: 2021
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DOI: 10.1038/s41467-021-23990-4

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