Brønsted acid-catalyzed intramolecular hydroamination of protected alkenylamines. Synthesis of pyrrolidines and piperidines.
[reaction: see text]. The cyclization of aminoalkenes bearing an electron-withdrawing group on the nitrogen atom was catalyzed by triflic or sulfuric acid in toluene. Pyrrolidines and piperidines were formed in excellent yields. N-phenylanilides also underwent cyclization to form gamma-lactams.
Schlummer
Björn
B
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.
Hartwig
John F
JF
D000475:Alkenes / Q000737:chemistry; D000586:Amination; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D008698:Mesylates / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis*; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013449:Sulfonamides / Q000737:chemistry; D014105:Tosyl Compounds / Q000737:chemistry
D000475:Alkenes; D000588:Amines; D007202:Indicators and Reagents; D008698:Mesylates; D011725:Pyridines; D011759:Pyrrolidines; D013449:Sulfonamides; D014105:Tosyl Compounds; C012077:trifluoromethanesulfonic acid