Enantioselective remote meta-C–H arylation and alkylation via a chiral transient mediator

Hang Shi, Alastair N. Herron, Ying Shao, Qian Shao and Jin-Quan Yu ()
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Hang Shi: The Scripps Research Institute
Alastair N. Herron: The Scripps Research Institute
Ying Shao: The Scripps Research Institute
Qian Shao: The Scripps Research Institute
Jin-Quan Yu: The Scripps Research Institute

Nature, 2018, vol. 558, issue 7711, 581-585

Abstract: Abstract Enantioselective carbon–hydrogen (C–H) activation reactions by asymmetric metallation could provide new routes for the construction of chiral molecules1,2. However, current methods are typically limited to the formation of five- or six-membered metallacycles, thereby preventing the asymmetric functionalization of C–H bonds at positions remote to existing functional groups. Here we report enantioselective remote C–H activation using a catalytic amount of a chiral norbornene as a transient mediator, which relays initial ortho-C–H activation to the meta position. This was used in the enantioselective meta-C–H arylation of benzylamines, as well as the arylation and alkylation of homobenzylamines. The enantioselectivities obtained using the chiral transient mediator are comparable across different classes of substrates containing either neutral σ-donor or anionic coordinating groups. This relay strategy could provide an alternative means to remote chiral induction, one of the most challenging problems in asymmetric catalysis3,4.

Date: 2018
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DOI: 10.1038/s41586-018-0220-1

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