Synfacts 2010(9): 1070-1070  
DOI: 10.1055/s-0030-1257967
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric One-Pot Aminofluorination of Enals

Contributor(s): Benjamin List, Steffen Müller
C. Appayee, S. E. Brenner-Moyer*
The City University of New York, Brooklyn, USA
Further Information

Publication History

Publication Date:
23 August 2010 (online)


The authors present an amination-fluorination cascade reaction of aliphatic enals. In the presence of prolinol silylether 1, Cbz-protected methoxyamine was found to be a suitable amine nucleophile for the 1,4-addition to the substrates. Later on the 1-derived enamine of the amination product could be further reacted with an electrophilic fluorine source to give, after reduction, the α-fluoro-β-amino alcohols in reasonable yields and good to excellent diastereoselectivities and enantioselectivities in a one-pot procedure.