title: A highly stereoselective Diels-Alder cycloaddition of enones with chiral cyclic 2-amidodienes derived from allenamides.
abstract: Lewis acid promoted Diels-Alder cycloadditions of a series of de novo chiral cyclic 2-amidodienes are described. These cyclic 2-amidodienes are derived from chiral α-allyl allenamides via a sequence of E-selective 1,3-H shift and 6π-electron pericyclic ring closure. With enones serving as effective dienophiles, these cycloadditions can be highly diastereoselective depending upon the chiral amide substituent, thereby representing a facile entry to optically enriched [2.2.2]bicyclic manifolds.
authors.affiliation: Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53705, United States.
authors.forename: Li-Chao
authors.initials: LC
authors.lastname: Fang
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung
authors.forename: Zhi-Xiong
authors.initials: ZX
authors.lastname: Ma
authors.forename: William R
authors.initials: WR
authors.lastname: Presser
mesh_terms: D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D061565:Cycloaddition Reaction; D004583:Electrons; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D000577:Amides; D058116:Lewis Acids