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. 2008 Dec 31;130(52):17638-9.
doi: 10.1021/ja806585m.

Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes

Peter H Fuller  1 , Jin-Woo Kim, Sherry R Chemler
Affiliations

Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes

Peter H Fuller et al. J Am Chem Soc. .

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.

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Figures

Scheme 1
Scheme 1
Transition state model and TEMPO functionalization
See this image and copyright information in PMC

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