Wilfried Raimondi

Highly Diastereo- and Enantioselective Organocatalytic Michael Addition of α-Ketoamides to Nitroalkenes

The first organocatalytic enantio- and diastereoselective conjugate addition of α-ketoamides to nitroalkenes has been achieved using a bifunctional amino thiourea catalyst. In this new approach, the substrate amide proton plays a critical role in the formation of the Michael anti-adducts in high yields and high stereoselectivities. To illustrate the high synthetic potential of this methodology, the diastereo- and enantioselective synthesis of a hexasubstituted cyclohexane via a Michael-Michael-Henry cascade reaction is described.

One-pot asymmetric cyclocarbohydroxylation sequence for the enantioselective synthesis of functionalised cyclopentanes

A new method has been developed for the enantioselective synthesis of highly functionalised cyclopentanes bearing up to three stereogenic centres with very high stereoselectivity. This one-pot process combines an enantioselective organocatalytic Michael addition with a highly diastereoselective [3+2]-cycloaddition-fragmentation step.