Kinetic resolution of cyclic benzylic azides enabled by site- and enantioselective C(sp3)–H oxidation

Pengbo Ye, Aili Feng, Lin Wang, Min Cao, Rongxiu Zhu and Lei Liu ()
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Pengbo Ye: School of Chemistry and Chemical Engineering, Shandong University
Aili Feng: School of Chemistry and Chemical Engineering, Shandong University
Lin Wang: School of Chemistry and Chemical Engineering, Shandong University
Min Cao: School of Chemistry and Chemical Engineering, Shandong University
Rongxiu Zhu: School of Chemistry and Chemical Engineering, Shandong University
Lei Liu: School of Chemistry and Chemical Engineering, Shandong University

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract Catalytic nonenzymatic kinetic resolution (KR) of racemates remains one of the most powerful tools to prepare enantiopure compounds, which dominantly relies on the manipulation of reactive functional groups. Moreover, catalytic KR of organic azides represents a formidable challenge due to the small size and instability of the azido group. Here, an effective KR of cyclic benzylic azides through site- and enantioselective C(sp3)–H oxidation is described. The manganese catalyzed oxidative KR reaction exhibits good functional group tolerance, and is applicable to a range of tetrahydroquinoline- and indoline-based organic azides with excellent site- and enantio-discrimination. Computational studies elucidate that the effective chiral recognition is derived from hydrogen bonding interaction between substrate and catalyst.

Date: 2022
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DOI: 10.1038/s41467-022-29319-z

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