Chiral Squaramide Derivatives Are Excellent Hydrogen Bond Donor Catalysts

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2008 Oct 14

PMID 18847268

Citations 83

Authors

Jeremiah P Malerich

Koji Hagihara

Viresh H Rawal

Affiliations

Soon will be listed here.

Abstract

Thioureas represent the dominant platform for hydrogen bond promoted asymmetric catalysts. A large number of reactions, reported in scores of publications, have been successfully promoted by chiral thioureas. The present paper reports the use of squaramides as a highly effective new scaffold for the development of chiral hydrogen bond donor catalysts. Squaramide catalysts are very simple to prepare. The (-)-cinchonine modified squaramide (5), easily prepared through a two-step process from methyl squarate, was shown to be an effective catalyst, even at catalyst loadings as low as 0.1 mol%, for the conjugate addition reactions of 1,3-dicarbonyl compounds to beta-nitrostyrenes. The addition products were obtained in high yields and excellent enantioselectivities.

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