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A series of simple 4-hydroxyprolinamides was synthesised and they were found to act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields (98%), with complete diastereoselectivity (99:1, syn:anti) and enantioselectivity (98% e.e. for syn). Furthermore, the use of low catalyst loadings (5 mol%) and a low aldehyde molar excess (1.5 equivalents) were achieved.
Kelleher, F., Watts, J., Luu, L., McKee, V., Carey, E.: Structure-reactivity Studies of Simple 4-hydroxyprolinamide Organocatalysts in the Asymmetric Michael Addition Reaction of Aldehydes to Nitroolefins. Advanced Synthesis and Catalysis, vol. 354 (6), p. 1035–1042, April 16, 2012.