Synfacts 2008(11): 1221-1221  
DOI: 10.1055/s-0028-1083386
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of N,O-Aminals

Contributor(s): Benjamin List, Steffen Müller
G. Li, F. R. Fronczek, J. C. Antilla*
University of South Florida, Tampa and Louisiana State University, Baton Rouge, USA
Further Information

Publication History

Publication Date:
23 October 2008 (online)

Significance

The organocatalytic enantioselective addition of alcohols to N-benzoylimines was achieved for the first time using chiral phosphoric acid catalysis. Aromatic and aliphatic im­ines reacted with branched and unbranched alcohols to give the corresponding N,O-aminals in good yields and enantioselectivities. Remarkably high enantiomeric ratios were obtained although the reaction proceeded in the same manner but racemic when no catalyst was present.