Axially chiral guanidine as highly active and enantioselective catalyst for electrophilic amination of unsymmetrically substituted 1,3-dicarbonyl compounds.

Masahiro Terada, Megumi Nakano, Hitoshi Ube

Index: J. Am. Chem. Soc. 128 , 16044, (2006)

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Abstract

A newly designed axially chiral guanidine is found to function as an effective platform for asymmetric induction at the alpha-carbon of unsymmetrically substituted 1,3-dicarbonyl compounds. Highly efficient and enantioselective electrophilic amination of various 1,3-dicarbonyl compounds with azodicarboxylate was successfully achieved using the present chiral guanidine catalyst, which provides efficient access to the construction of nitrogen-substituted quaternary stereocenters in an optically active form.