CpIr complex-catalyzed N-heterocyclization of primary amines with diols: a new catalytic system for environmentally benign synthesis of cyclic amines.
[reaction: see text] A new efficient method for the N-heterocyclization of primary amines with diols catalyzed by a CpIr complex was developed. A variety of five-, six-, and seven-membered cyclic amines were synthesized in good to excellent yields with the formation of only water as a byproduct. A two-step asymmetric synthesis of (S)-2-phenylpiperidine was also achieved using (R)-1-phenylethylamine as a starting primary amine.
Fujita
Ken-Ichi
K
Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan. fujitak@kagaku.mbox.media.kyoto-u.ac.jp
Fujii
Takeshi
T
Yamaguchi
Ryohei
R
D000438:Alcohols / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D000588:Amines; D007202:Indicators and Reagents