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Organocatalytic asymmetric synthesis of β,β-diaryl ketones via one-pot tandem dehydration/1,6-addition/decarboxylation transformation of β-keto acids and 4-hydroxybenzyl alcohols

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Abstract

Herein we describe an organocatalytic protocol for the asymmetric synthesis of β,β-diaryl ketones. Under the catalysis of a chiral phosphoric acid, 4-hydroxybenzyl alcohols underwent dehydration to form para-quinone methides, which reacted with β-keto acids in 1,6-addition reactions. Upon treatment with Et3N in one-pot, decarboxylation proceeded to provide the desired chiral ketones in nearly quantitative yields with high enantioselectivities.

Graphical abstract: Organocatalytic asymmetric synthesis of β,β-diaryl ketones via one-pot tandem dehydration/1,6-addition/decarboxylation transformation of β-keto acids and 4-hydroxybenzyl alcohols

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Article information


Submitted
26 Mar 2020
Accepted
24 Jun 2020
First published
24 Jun 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Organocatalytic asymmetric synthesis of β,β-diaryl ketones via one-pot tandem dehydration/1,6-addition/decarboxylation transformation of β-keto acids and 4-hydroxybenzyl alcohols

J. Niu, J. Nie, S. Li and J. Ma, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02213F

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