Synfacts 2007(5): 0539-0539  
DOI: 10.1055/s-2007-968401
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Asymmetric Conjugate Addition of N-Heterocycles to Enals

Contributor(s): Benjamin List, Subhas Chandra Pan
P. Dinér, M. Nielsen, M. Marigo, K. A. Jørgensen
Aarhus University, Denmark
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Publication History

Publication Date:
24 April 2007 (online)


An organocatalytic asymmetric conjugate addition of N-heterocycles to α,β-unsaturated aldehydes has been described. The N-heterocycles investigated were 1,2,4-triazole, 5-phenyl tetrazole, 1,2,3-benzotriazole, and 1,2,3-triazole. Proline-derived catalyst 1 in combination with PhCO2H has been found to be effective for this reaction. With 10 mol% of the catalyst 1 moderate to high yields (45-87%) and high enantioselectivities (er = 90:10 to 97:3) were obtained for different alkyl and alkenyl substituted enals.