Structure-reactivity Studies of Simple 4-hydroxyprolinamide Organocatalysts in the Asymmetric Michael Addition Reaction of Aldehydes to Nitroolefins

Authors

Fintan Kelleher, Technological University DublinFollow
John Watts, Technological University Dublin
Lien Luu, Technological University Dublin
Vickie McKee, Loughborough University
Ed Carey, Technological University Dublin

Document Type

Article

Rights

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

Disciplines

Organic Chemistry

Publication Details

Advanced Synthesis and Catalysis

Volume 354, Issue 6, pages 1035–1042, April 16, 2012

Abstract

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.

Recommended Citation

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.

Funder

Irish Government’s National Development Plan