title: An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts.
abstract: Preparations of de novo acyclic 2-amido-dienes and 3-amido-trienes through 1,3-hydrogen shifts from allenamides are described. These 1,3-hydrogen shifts could be achieved thermally or they could be promoted by the use of Brønsted acids. Under either condition, these processes are highly regioselective in favour of the α-position, and highly stereoselective in favour of the E-configuration. In addition, 6π-electron electrocyclic ring-closure could be carried out with 3-amido-trienes to afford cyclic 2-amido-dienes, and such electrocyclic ring-closure could be rendered in tandem with the 1,3-hydrogen shift.
authors.affiliation: Department of Chemistry and Division of Pharmaceutical Sciences, University of Wisconsin, Madison, WI 53705.
authors.forename: Ryuji
authors.initials: R
authors.lastname: Hayashi
authors.forename: John B
authors.initials: JB
authors.lastname: Feltenberger
authors.forename: Andrew G
authors.initials: AG
authors.lastname: Lohse
authors.forename: Mary C
authors.initials: MC
authors.lastname: Walton
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung