Gold(I)-catalysed alcohol additions to cyclopropenes.
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.
Hadfield
Maximillian S
MS
School of Engineering and Physical Sciences, Chemistry-William H. Perkin Building, Heriot-Watt University, Edinburgh, UKEH14 4AS.
Bauer
Jürgen T
JT
Glen
Pauline E
PE
Lee
Ai-Lan
AL
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
D000438:Alcohols; D003521:Cyclopropanes; D004987:Ethers; D050607:Organogold Compounds; D006046:Gold; C021985:cyclopropene