Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes.
The copper-catalyzed enantioselective intramolecular aminooxygenation of alkenes is reported herein. This is the first report of an enantioselective intramolecular alkene aminooxygenation process. N-Arylsulfonyl-2-allylanilines and 4-pentenylarylsulfonamides cyclize in high yield and with good enantioselectivity, providing new chiral methyleneoxy-functionalized dihydroindolines and pyrrolidines. Tetramethylaminopyridyl radical (TEMPO) serves as both the source of the oxygen and the stoichiometric oxidant. These reactions are catalyzed by copper(II) triflate, complexed with (4S,5R)-Bis-Phbox. The unprotected aminoalcohols can be obtained by sequential dissolving metal reductions of the N-S and O-N bonds.
Fuller
Peter H
PH
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260, USA.
Kim
Jin-Woo
JW
Chemler
Sherry R
SR
D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis*; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry
D000475:Alkenes; D000588:Amines; D000814:Aniline Compounds; D007211:Indoles; D016877:Oxidants; D011759:Pyrrolidines; D013449:Sulfonamides; D003300:Copper