Axially chiral guanidine as highly active and enantioselective catalyst for electrophilic amination of unsymmetrically substituted 1,3-dicarbonyl compounds.
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.
Terada
Masahiro
M
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. mterada@mail.tains.tohoku.ac.jp
Nakano
Megumi
M
Ube
Hitoshi
H
D000586:Amination; D002384:Catalysis; D004583:Electrons; D019791:Guanidine / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D019791:Guanidine