Organocatalytic discrimination of non-directing aryl and heteroaryl groups: enantioselective synthesis of bioactive indole-containing triarylmethanes

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

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Author(s)

  • Qiaolin Yan
  • Meng Duan
  • Peiyuan Yu
  • K. N. Houk
  • Jianwei Sun

Detail(s)

Original languageEnglish
Article number5767
Journal / PublicationChemical Science
Volume13
Issue number19
Online published13 Apr 2022
Publication statusPublished - 21 May 2022

Link(s)

Abstract

Despite the enormous developments in asymmetric catalysis, the basis for asymmetric induction is largely limited to the spatial interaction between the substrate and catalyst. Consequently, asymmetric discrimination between two sterically similar groups remains a challenge. This is particularly formidable for enantiodifferentiation between two aryl groups without a directing group or electronic manipulation. Here we address this challenge by using a robust organocatalytic system leading to excellent enantioselection between aryl and heteroaryl groups. With versatile 2-indole imine methide as the platform, an excellent combination of a superb chiral phosphoric acid and the optimal hydride source provided efficient access to a range of highly enantioenriched indole-containing triarylmethanes. Control experiments and kinetic studies provided important insights into the mechanism. DFT calculations also indicated that while hydrogen bonding is important for activation, the key interaction for discrimination of the two aryl groups is mainly π-π stacking. Preliminary biological studies also demonstrated the great potential of these triarylmethanes for anticancer and antiviral drug development.

Research Area(s)

  • ASYMMETRIC TRANSFER HYDROGENATION, CHIRAL BRONSTED ACID, HANTZSCH ESTERS, KETONES, BENZOTHIAZOLINE, BENZOPHENONES, PHOSPHORAMIDE, CONSTRUCTION, BENZHYDROLS, STRATEGIES

Citation Format(s)

Organocatalytic discrimination of non-directing aryl and heteroaryl groups: enantioselective synthesis of bioactive indole-containing triarylmethanes. / Yan, Qiaolin; Duan, Meng; Chen, Cien et al.
In: Chemical Science, Vol. 13, No. 19, 5767, 21.05.2022.

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

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