Issue 4, 2019

Organocatalytic atropo- and E/Z-selective Michael addition reaction of ynones with α-amido sulfones as sulfone-type nucleophile

Abstract

We describe herein the first enantioselective organocatalytic Michael addition reaction of α-amido sulfones to ynones to access axially chiral styrenes. Sulfone-containing axially chiral styrene compounds were constructed with excellent enantioselectivity and almost complete E/Z-selectivity (up to 97% ee, >20 : 1 E/Z) in the presence of an easily accessible cinchona-alkaloid-derived multiple hydrogen-bonding catalyst. The enantioenriched sulfone-containing products were used as precursors for further transformations without any loss of the ee value. The equilibration process of this transformation was monitored by 1H NMR spectroscopy.

Graphical abstract: Organocatalytic atropo- and E/Z-selective Michael addition reaction of ynones with α-amido sulfones as sulfone-type nucleophile

Supplementary files

Article information

Article type
Research Article
Submitted
14 Nov 2018
Accepted
16 Dec 2018
First published
18 Dec 2018

Org. Chem. Front., 2019,6, 451-455

Organocatalytic atropo- and E/Z-selective Michael addition reaction of ynones with α-amido sulfones as sulfone-type nucleophile

N. Zhang, T. He, Y. Liu, S. Li, Y. Tan, L. Peng, D. Li, C. Shan and H. Yan, Org. Chem. Front., 2019, 6, 451 DOI: 10.1039/C8QO01241E

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