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. 2019 Aug 14;9(44):25377-25381.
doi: 10.1039/c9ra04836g. eCollection 2019 Aug 13.

Chiral benzene backbone-based sulfoxide-olefin ligands for highly enantioselective Rh-catalyzed addition of arylboronic acids to N-tosylarylimines

Feng Xue  1 , Qibin Liu  2 , Yong Zhu  1 , Yunfei Qing  1 , Boshun Wan  3
Affiliations

Chiral benzene backbone-based sulfoxide-olefin ligands for highly enantioselective Rh-catalyzed addition of arylboronic acids to N-tosylarylimines

Feng Xue et al. RSC Adv. .

Abstract

An efficient Rh-catalyzed addition of arylboronic acids to N-tosylarylimines has been developed with chiral benzene backbone-based sulfoxide-olefin ligands, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have shown to be more effective. The versatile method tolerates a wide range of functional groups and shows broad scope without regard to electronic or steric substitution pattern, allowing access to a broad range of chiral diarylmethylamines in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee).

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Rh-catalyzed asymmetric arylation of N-tosylarylimines.
Fig. 1
Fig. 1. Proposed stereochemical pathway for the asymmetric arylation.
See this image and copyright information in PMC

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