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Issue 23, 2018
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Enantioselective synthesis of chiral oxazolines from unactivated ketones and isocyanoacetate esters by synergistic silver/organocatalysis

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Abstract

A multicatalytic approach that combines a bifunctional Brønsted base–squaramide organocatalyst and Ag+ as Lewis acid has been applied in the reaction of unactivated ketones with tert-butyl isocyanoacetate to give chiral oxazolines bearing a quaternary stereocenter. The formal [3+2] cycloaddition provided high yields of the corresponding cis-oxazolines with good diastereoselectivity and excellent enantioselectivity, being applied to aryl–alkyl and alkyl–alkyl ketones.

Graphical abstract: Enantioselective synthesis of chiral oxazolines from unactivated ketones and isocyanoacetate esters by synergistic silver/organocatalysis

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Supplementary files

Article information


Submitted
31 Jan 2018
Accepted
20 Feb 2018
First published
20 Feb 2018

Chem. Commun., 2018,54, 2862-2865
Article type
Communication

Enantioselective synthesis of chiral oxazolines from unactivated ketones and isocyanoacetate esters by synergistic silver/organocatalysis

P. Martínez-Pardo, G. Blay, M. C. Muñoz, J. R. Pedro, A. Sanz-Marco and C. Vila, Chem. Commun., 2018, 54, 2862
DOI: 10.1039/C8CC00856F

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