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Synfacts 2006(3): 0282-0282
DOI: 10.1055/s-2006-931986
DOI: 10.1055/s-2006-931986
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York
Enantioselective Nitroaldol Reaction of α-Keto-esters Catalyzed by Cinchona Alkaloids
H. Li, B. Wang, L. Deng*
Brandeis University, Waltham, USA
Further Information
Publication History
Publication Date:
21 February 2006 (online)
Significance
The authors report an enantioselective organocatalytic nitroaldol reaction of α-ketoesters. Bifunctional monomeric C6′-OH cinchona alkaloids were found to be effective catalysts for the 1,2-additions to carbonyls. With 5 mol% of catalyst 1 high yields (86-98%) and excellent enantioselectivities (93-97%) are obtained for a wide range of α-ketoesters. High chemoselectivities (>95:5) have also been attained for the challenging alkenyl α-ketoesters.