title: Asymmetric synthesis of carbocycles: use of intramolecular conjugate displacement.
abstract: Intramolecular conjugate displacement (ICD), the process illustrated in , has been applied to the Morita-Baylis-Hillman adducts formed from (5S)-5-(l-menthyloxy)-2(5H)-furanone and aldehydes that are substituted in the γ- or δ-position by geminal phenylthio groups. When the initial Morita-Baylis-Hillman alcohols are acetylated and oxidized to geminal sulfones, deprotonation causes ring closure by ICD (2.5→2.6). Hydrogenation, DIBAL-H reduction and desulfonylation releases an optically pure carbocycle.
authors.affiliation: Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Dinesh T
authors.initials: DT
authors.lastname: Sreedharan
authors.forename: Derrick L J
authors.initials: DL
authors.lastname: Clive
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000438:Alcohols; D006844:Hydrocarbons, Cyclic; D013450:Sulfones