Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates.
Treatment of the N-4,5-hexadienyl carbamate 2a with a catalytic 1:2 mixture of [(S)-1]Au2Cl2 [(S)-1 = (S)-3,5-t-Bu-4-MeO-MeOBIPHEP] and AgClO4 in m-xylene at -40 degrees C for 24 h led to isolation of 2-vinylpyrrolidine 3a in 97% yield with 81% ee. Gold(I)-catalyzed enantioselective hydroamination was effective for a number of carbamate groups and tolerated terminal disubstitutution of the allenyl moiety.
Zhang
Zhibin
Z
Duke University, French Family Science Center, Durham, North Carolina 27708-0346, USA.
Bender
Christopher F
CF
Widenhoefer
Ross A
RA
D000586:Amination; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D013237:Stereoisomerism
D002219:Carbamates; D006046:Gold