ol202276h_si_002.cif (18.13 kB)

Diastereoselective Control of Intramolecular Aza-Michael Reactions Using Achiral Catalysts

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posted 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.