Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.
Treatment of 2-allenyl indole 4 with a catalytic 1:2 mixture of [(S)-2]Au2Cl2 [(S)-2 = (S)-3,5-tBu-4-MeO-MeOBIPHEP] and AgBF4 in toluene at -10 degrees C for 17 h led to isolation of tetrahydrocarbazole 5 in 88% yield with 92% ee. The protocol was effective for the cyclization of terminally disubstituted allenes and for the formation of seven-membered rings.
Liu
Cong
C
Duke University, French Family Science Center, Durham, NC 27708-0346, USA.
Widenhoefer
Ross A
RA
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D012834:Silver / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism
D000466:Alkadienes; D007211:Indoles; D008024:Ligands; D012997:Solvents; D012834:Silver; C025947:propadiene; D006046:Gold; D006859:Hydrogen