Structure-Reactivity Relationships of L-Proline Derived Spirolactams and a-Methyl Prolinamide Organocatalysts in the Asymmetric Michael Addition Reaction of Aldehydes to Nitroolefins.

Authors

Fintan Kelleher, Technological University DublinFollow
Sinead Kelly, Technological University Dublin
John Watts, Technological University Dublin
Vickie McKee, Loughborough University

Document Type

Article

Rights

Available under a Creative Commons Attribution Non-Commercial Share Alike 4.0 International Licence

Disciplines

Organic Chemistry

Publication Details

Tetrahedron Volume 66, Issue 19, 8 May 2010, Pages 3525–3536.

Abstract

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.

Recommended Citation

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 ...

Funder

Irish Government