Issue 30, 2018

N-Heterocyclic carbenes as chiral Brønsted base catalysts: a highly diastereo- and enantioselective 1,6-addition reaction

Abstract

Highly diastereo- and enantioselective 1,6-addition of 1,3-ketoamides to p-quinone methides (p-QMs) using chiral NHCs as Brønsted base catalysts is developed. The reaction is based on the utilization of a 1,3-ketoamide having acidic N–H that forms a chiral ion-pair consisting of the enolate and the azolium ion. Different β-ketoamides and functionalized p-QMs are applicable to the reaction. Synthetic application of the method is demonstrated via the preparation of highly enantioenriched β and γ-lactam derivatives.

Graphical abstract: N-Heterocyclic carbenes as chiral Brønsted base catalysts: a highly diastereo- and enantioselective 1,6-addition reaction

Supplementary files

Article information

Article type
Edge Article
Submitted
15 5 2018
Accepted
01 7 2018
First published
02 7 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 6446-6450

N-Heterocyclic carbenes as chiral Brønsted base catalysts: a highly diastereo- and enantioselective 1,6-addition reaction

S. Santra, A. Porey, B. Jana and J. Guin, Chem. Sci., 2018, 9, 6446 DOI: 10.1039/C8SC02138D

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