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Issue 21, 2020
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A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

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Abstract

An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported. Both enantiomers of the Michael adducts can be obtained in high enantioselectivity and good yield merely by changing the solvent. The origin of the chirality switch in the products was examined in each solvent via spectroscopic analyses.

Graphical abstract: A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

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Article information


Submitted
25 Mar 2020
Accepted
14 May 2020
First published
14 May 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 5572-5576
Article type
Edge Article

A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

N. Hayama, Y. Kobayashi, E. Sekimoto, A. Miyazaki, K. Inamoto, T. Kimachi and Y. Takemoto, Chem. Sci., 2020, 11, 5572
DOI: 10.1039/D0SC01729A

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