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 may. 2018
Accepted
01 jul. 2018
First published
02 jul. 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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