Aerobic hydroxylation of N-borylenamine: triethylborane-mediated hydroxyalkylation of alpha,beta-unsaturated oxime ether.
Intermolecular hydroxyalkylation of alpha,beta-unsaturated imines involving Et3B-mediated regioselective alkyl radical addition and subsequent hydroxylation with molecular oxygen has been developed, in which N-borylenamine generated by trapping of the enaminyl radical with Et3B was a key intermediate in the proposed aerobic hydroxylation mechanism.
Ueda
Masafumi
M
Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
Miyabe
Hideto
H
Kimura
Takahiro
T
Kondoh
Eiko
E
Naito
Takeaki
T
Miyata
Okiko
O
D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D006900:Hydroxylation; D007097:Imines / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D013237:Stereoisomerism; D014050:Toluene / Q000737:chemistry
D000588:Amines; D001880:Boranes; D001896:Boron Compounds; D007097:Imines; D014050:Toluene; D010100:Oxygen; C079756:triethylborane