Issue 7, 2018

N-Heterocyclic carbene promoted enantioselective desymmetrization reaction of diarylalkane-bisphenols

Abstract

An enantioselective NHC-catalyzed desymmetrization reaction of diarylalkane-bisphenols with aldehydes was reported with linear free energy relationships (LFERs) to correlate the enantioselectivities with the steric and electronic parameters. The reaction scope is substantial, and a wide range of aromatic and aliphatic aldehydes, as well as diarylalkane-bisphenols were tolerated under the reaction conditions. As a result, a series of diarylalkane-bisphenol products were generated with excellent reactivities and enantioselectivities (up to 99% yield and up to 98.7 : 1.3 er). Furthermore, the reaction can be scaled up, and the desired product can be easily converted to valuable structures.

Graphical abstract: N-Heterocyclic carbene promoted enantioselective desymmetrization reaction of diarylalkane-bisphenols

Supplementary files

Article information

Article type
Research Article
Submitted
02 dec 2017
Accepted
11 jan 2018
First published
12 jan 2018

Org. Chem. Front., 2018,5, 1101-1107

N-Heterocyclic carbene promoted enantioselective desymmetrization reaction of diarylalkane-bisphenols

S. Li, B. Liu, L. Chen, X. Li and J. Cheng, Org. Chem. Front., 2018, 5, 1101 DOI: 10.1039/C7QO01083D

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