Enantioselective Michael reactions catalyzed by a chiral bicyclic guanidine

ORGN 22

Choon-Hong Tan, chmtanch@nus.edu.sg and Weiping Ye, g0306090@nus.edu.sg. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
Asymmetric Michael reactions catalyzed by a chiral bicyclic guanidine are described. A variety of 1,3-dicarbonyl compounds, including S,S'-dialkyl dithiomalonates, dialkyl malonates, 1,3-diketones and benzoylacetate, can function as the Michael donors in the reaction with various N-alkyl maleimides and 2-cyclopenten-1-one, giving high enantioselectivities and yields.