title: A tandem cross-metathesis/semipinacol rearrangement reaction.
abstract: An efficient and (E)-selective synthesis of a 6-alkylidenebicyclo[3.2.1]octan-8-one has been developed. The key step is a tandem cross-metathesis/semipinacol rearrangement reaction, wherein the Hoveyda-Grubbs II catalyst, or more likely a derivative thereof, serves as the Lewis acid for the rearrangement. Despite the fact that both the starting alkene and the cross-metathesis product are viable rearrangement substrates, only the latter rearranges, suggesting that the Lewis acidic species is generated only after the cross-metathesis reaction is complete.
authors.affiliation: Department of Chemistry, Columbia University , New York, New York 10027, United States.
authors.forename: Christopher W
authors.initials: CW
authors.lastname: Plummer
authors.forename: Arash
authors.initials: A
authors.lastname: Soheili
authors.forename: James L
authors.initials: JL
authors.lastname: Leighton
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D053138:Cyclohexenes / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001643:Bridged Bicyclo Compounds; D053138:Cyclohexenes; D058116:Lewis Acids; C519041:semipinacol