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L-Proline derived spirolactams and a-methyl prolinamides act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields, with good diastereoselectivity and enantioselectivity. Furthermore, low catalyst loadings (5 mol%) and a low aldehyde molar excess (1.5 molar equivalents) were achieved.
Kelleher, F., Kelly, S., Watts, J. and McKee, V. Structure-reactivity relationships of L-proline derived spirolactams and a-methyl prolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins. Tetrahedron Volume 66, Issue 19, 8 May 2010, Pages 3525–3536. DOI: 10.1016/j.tet.2010.03.002 ...