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Organocatalytic asymmetric cascade 1,6-addition/hemiketalization/retro-Henry reaction of ortho-hydroxyphenyl-substituted p-QMs with α-nitroketones

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Abstract

A novel organocatalytic asymmetric cascade 1,6-addition/hemiketalization/retro-Henry reaction of ortho-hydroxyphenyl-substituted p-QMs with α-nitroketones is described. A variety of novel chiral 2-(1-(4-hydroxyphenyl)ethyl)phenols are constructed for the first time with high yields (up to 92%) and excellent enantioselectivities (up to >99% ee) under mild reaction conditions. A gram-scale experiment of this process is also presented.

Graphical abstract: Organocatalytic asymmetric cascade 1,6-addition/hemiketalization/retro-Henry reaction of ortho-hydroxyphenyl-substituted p-QMs with α-nitroketones

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Submitted
23 Feb 2020
Accepted
13 Mar 2020
First published
13 Mar 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Organocatalytic asymmetric cascade 1,6-addition/hemiketalization/retro-Henry reaction of ortho-hydroxyphenyl-substituted p-QMs with α-nitroketones

J. Zhou, L. Bai, G. Liang, Q. Xu, L. Zhou and H. Zhou, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00397B

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