Issue 49, 2022

Isothiourea-catalyzed formal enantioselective conjugate addition of benzophenone imines to β-fluorinated α,β-unsaturated esters

Abstract

The isothiourea-catalyzed formal enantioselective conjugate addition of 2-hydroxybenzophenone imine derivatives to α,β-unsaturated para-nitrophenyl esters has been developed. Investigations of the scope and limitations of this procedure showed that β-electron withdrawing substituents within the α,β-unsaturated ester component are required for good product yield, giving rise to a range of β-imino ester and amide derivatives in moderate to good isolated yields with excellent enantioselectivity (20 examples, up to 81% yield and 97 : 3 er).

Graphical abstract: Isothiourea-catalyzed formal enantioselective conjugate addition of benzophenone imines to β-fluorinated α,β-unsaturated esters

Supplementary files

Article information

Article type
Communication
Submitted
04 4月 2022
Accepted
20 5月 2022
First published
20 5月 2022
This article is Open Access
Creative Commons BY license

Chem. Commun., 2022,58, 6886-6889

Isothiourea-catalyzed formal enantioselective conjugate addition of benzophenone imines to β-fluorinated α,β-unsaturated esters

J. E. Lapetaje, C. M. Young, C. Shu and A. D. Smith, Chem. Commun., 2022, 58, 6886 DOI: 10.1039/D2CC01936A

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