Regio- and stereoselective synthesis of alkyl allylic ethers via gold(I)-catalyzed intermolecular hydroalkoxylation of allenes with alcohols.
Reaction of 1-phenyl-1,2-butadiene with 2-phenyl-1-ethanol catalyzed by a 1:1 mixture of a gold(I) N-heterocyclic carbene complex and AgOTf at room temperature for 1 h led to isolation of (E)-(3-phenethoxy-1-butenyl)benzene in 96% yield as a single regio- and stereoisomer. Gold(I)-catalyzed intermolecular allene hydroalkoxylation was effective for monosubsituted, 1,1- and 1,3-disubstituted, trisubstituted, and tetrasubstituted allenes and for a range of primary and secondary alcohols, methanol, phenol, and propionic acid.
Zhang
Zhibin
Z
Duke University, French Family Science Center, Durham, North Carolina 27708-0346, USA.
Widenhoefer
Ross A
RA
D000438:Alcohols / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000478:Alkylation; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D000475:Alkenes; D004987:Ethers; D009942:Organometallic Compounds; D012834:Silver; D006046:Gold