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.
UMR CNRS 6263 iSm2, Aix-Marseille Université, Centre Saint Jérôme, service 531, 13397 Marseille, France.
Olivier
O
Baslé
Wilfried
W
Raimondi
Maria Del Mar Sanchez
Mdel M
Duque
Damien
D
Bonne
Thierry
T
Constantieux
Jean
J
Rodriguez