title: Gold(I)-catalysed alcohol additions to cyclopropenes.
abstract: Gold(i)-catalysed addition of alcohols to 3,3-disubstituted cyclopropenes occurs in a highly regioselective and facile manner to produce alkyl tert-allylic ethers in good yields. The reaction is tolerant of sterically hindered substituents on the cyclopropene as well as primary and secondary alcohols as nucleophiles. In this full article, we report on the substrate scope and plausible mechanism, as well as the regioselectivity issues arising from subsequent gold(i)-catalysed isomerisation of tertiary to primary allylic ethers.
authors.affiliation: School of Engineering and Physical Sciences, Chemistry-William H. Perkin Building, Heriot-Watt University, Edinburgh, UKEH14 4AS.
authors.forename: Maximillian S
authors.initials: MS
authors.lastname: Hadfield
authors.forename: Jürgen T
authors.initials: JT
authors.lastname: Bauer
authors.forename: Pauline E
authors.initials: PE
authors.lastname: Glen
authors.forename: Ai-Lan
authors.initials: AL
authors.lastname: Lee
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D050607:Organogold Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D003521:Cyclopropanes; D004987:Ethers; D050607:Organogold Compounds; D006046:Gold; C021985:cyclopropene