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Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes.

ABSTRACT: 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.

SUBMITTER: Fuller PH

PROVIDER: S-EPMC2674573 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes.

Fuller Peter H PH Kim Jin-Woo JW Chemler Sherry R SR

Journal of the American Chemical Society 20081201 52

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 stoichiometri ...[more]

PMID: 19049311

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