NHC-Catalyzed Atroposelective Acylation of Phenols: Access to Enantiopure NOBIN Analogs by Desymmetrization

Org Lett. 2019 Aug 2;21(15):6169-6172. doi: 10.1021/acs.orglett.9b02425. Epub 2019 Jul 24.

Abstract

Herein we present a highly efficient N-heterocyclic-carbene (NHC)-catalyzed atroposelective acylation of amino bisphenols to provide access to a wide range of 1,1'-biaryl-2,2'-amino alcohols (NOBIN analogs) in high yield and with uniformly excellent enantioselectivity. This catalytic system is shown to proceed through a combination of desymmetrization and secondary kinetic resolution to produce the axially chiral products in excellent enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't