title: Diastereoselective control of intramolecular aza-Michael reactions using achiral catalysts.
abstract: 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.
authors.affiliation: Chemical Biology Program, Broad Institute of Harvard and MIT, 7 Cambridge Center, Cambridge, Massachusetts 02142, USA.
authors.forename: Cheng
authors.initials: C
authors.lastname: Zhong
authors.forename: Yikai
authors.initials: Y
authors.lastname: Wang
authors.forename: Alvin W
authors.initials: AW
authors.lastname: Hung
authors.forename: Stuart L
authors.initials: SL
authors.lastname: Schreiber
authors.forename: Damian W
authors.initials: DW
authors.lastname: Young
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D002219:Carbamates; D007659:Ketones; D010165:Palladium