Synfacts 2006(2): 0169-0169  
DOI: 10.1055/s-2005-924800
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Asymmetric Aza-Henry Reaction

Contributor(s): Benjamin List, Daniela Kampen
C. Palomo*, M. Oiarbide, A. Laso, R. López
Universidad del País Vasco, San Sebastián, Spain
Further Information

Publication History

Publication Date:
23 January 2006 (online)

Significance

An organocatalytic asymmetric aza-Henry reaction has been described. Imines, generated in situ from α-amido sulfones 1, react with nitromethane and cesium hydroxide in the presence of 12 mol% of a chiral quininium salt 2 to give protected nitroamines 3. Linear and branched alkyl substrates, as well as aryl precursors provide the products in good yields and enantioselectivities. Furthermore, nitroethane can also be used yielding the corresponding products 4 in high syn/anti ratios and similarly good enan­tioselectivities.