Synlett 2008(11): 1661-1664  
DOI: 10.1055/s-2008-1078495
LETTER
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Direct Mannich Reaction Catalyzed by Chiral Brønsted Acid via Activation of Enecarbamate as an Aliphatic Imine Alternative

Masahiro Terada*, Hiroyasu Tanaka, Keiichi Sorimachi
Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan
Fax: +81(22)7956602; e-Mail: mterada@mail.tains.tohoku.ac.jp;
Further Information

Publication History

Received 13 April 2008
Publication Date:
11 June 2008 (online)

Abstract

An enantioselective direct Mannich reaction of acetyl­acetone with enecarbamates via protonation by a chiral monophosphoric acid catalyst is achieved, demonstrating the utility of in situ generation of unstable aliphatic imines.