Diastereoselective Control of Intramolecular Aza-Michael Reactions Using Achiral Catalysts
journal contributionposted on 21.10.2011, 00:00 by Cheng Zhong, Yikai Wang, Alvin W. Hung, Stuart L. Schreiber, Damian W. Young
An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to result in 3,5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were obtained selectively using chiral substrates and an achiral Pd (II) complex or strong Brønsted acid catalysis. A range of substrates undergoes these selective transformations. Functionalization of the resulting products yielding bicyclic heterocycles is also demonstrated.