Catalytic enantioselective synthesis of chiral tetraarylmethanes

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

71 Scopus Citations
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Author(s)

  • Xingguang Li
  • Meng Duan
  • Qianzhen Shao
  • Min Chen
  • K. N. Houk
  • Jianwei Sun

Related Research Unit(s)

Detail(s)

Original languageEnglish
Pages (from-to)1010-1019
Journal / PublicationNature Catalysis
Volume3
Issue number12
Online published14 Dec 2020
Publication statusPublished - Dec 2020

Abstract

While synthetic chemistry has experienced substantial development in the past century, challenges still remain to fully satisfy the needs in drug development. A bias in sampling linear and disc-shaped molecules in drug discovery over spherical ones has existed due to the lack of efficient access to the latter chemical space. Specifically, efficient strategies to synthesize tetraarylmethanes, a unique family of spherical molecules, has remained scarce. In particular, there has been essentially no efficient asymmetric synthesis of chiral tetraarylmethanes due to the overwhelming steric congestion and challenging stereocontrol encountered in assembly of the all-aryl-substituted quaternary stereocentre. Here we disclose an efficient catalytic synthesis of chiral tetraarylmethanes with high enantioselectivity via a stereoconvergent formal nucleophilic substitution reaction. Control experiments and density functional theory calculations provided strong support on hydrogen bonding interactions as the key elements to successful stereocontrol. The obtained enantioenriched products showed impressive preliminary anticancer activities.

Citation Format(s)

Catalytic enantioselective synthesis of chiral tetraarylmethanes. / Li, Xingguang; Duan, Meng; Deng, Zhiqin et al.
In: Nature Catalysis, Vol. 3, No. 12, 12.2020, p. 1010-1019.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review