Journal of the American Chemical Society 2006-12-20

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)

Full Text: HTML

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.

Related Compounds

Structure Name/CAS No. Articles
Di-tert-Butyl azodicarboxylate Structure Di-tert-Butyl azodicarboxylate
CAS:870-50-8