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Access to Enantiopure Triarylmethanes and 1,1‐Diarylalkanes by NHC‐Catalyzed Acylative Desymmetrization
Author(s) -
Lu Shenci,
Song Xiaoxiao,
Poh Si Bei,
Yang Hui,
Wong Ming Wah,
Zhao Yu
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605445
Subject(s) - desymmetrization , chemistry , enantiopure drug , carbene , enantioselective synthesis , intramolecular force , steric effects , catalysis , combinatorial chemistry , hydrogen bond , stereochemistry , selectivity , naphthalene , organic chemistry , molecule
We present herein an unprecedented, efficient and enantioselective synthesis of triarylmethanes and 1,1‐diarylalkanes through N‐heterocyclic carbene‐catalyzed acylative desymmetrization of bisphenols. This method utilizes readily available substrates, reagents and a simple procedure to deliver the valuable products in excellent enantiopurity. DFT calculations reveal that the selectivity is governed by the C−C bond cleavage step of the tetrahedral intermediate leading to the ester product. A transition state model featuring a combination of intramolecular hydrogen bond and steric effect is developed to explain the enantioselectivity.