title: Transfer of chirality in the rhodium-catalyzed intramolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and alkynes: synthesis of enantioenriched bicyclo[5.3.0]decatrienes.
abstract: Chiral bicycles: Enantioenriched bicyclo[5.3.0]decatrienes were prepared from readily available chiral 3-acyloxy-1,4-enynes (ACEs) for the first time. In most cases, the chirality of the ACEs could be transferred to the bicyclic products with high efficiency. Inversion of the configuration was observed, thus confirming the predictions of previous computational studies.
authors.affiliation: School of Pharmacy, University of Wisconsin, Madison, WI 53705-2222 (USA).
authors.forename: Xing-Zhong
authors.initials: XZ
authors.lastname: Shu
authors.forename: Casi M
authors.initials: CM
authors.lastname: Schienebeck
authors.forename: Wangze
authors.initials: W
authors.lastname: Song
authors.forename: Ilia A
authors.initials: IA
authors.lastname: Guzei
authors.forename: Weiping
authors.initials: W
authors.lastname: Tang
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D012238:Rhodium
keywords: catalysis; enynes; polycyclic compounds; rhodium; stereospecific reactions