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Stereoselective Copper-Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity.

ABSTRACT: A new protocol for diastereoselective copper-catalyzed intra-molecular alkene aminooxygenation, which provides methyleneoxy-functionalized disubstituted pyrrolidines and five-membered cyclic ureas from the corresponding ?-alkenyl sulfonamides and N-allylureas, is reported. In addition, some success was achieved in enantioselective desymmetrizations reactions. We discovered that the level of enantioselectivity and diastereoselectivity could be tuned by choice of copper(II) ligands and substrate N-substituent.

SUBMITTER: Paderes MC

PROVIDER: S-EPMC3153067 | biostudies-literature | 2011 Jul

REPOSITORIES: biostudies-literature

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Stereoselective Copper-Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity.

Paderes Monissa C MC Chemler Sherry R SR

European journal of organic chemistry 20110701 20-21

A new protocol for diastereoselective copper-catalyzed intra-molecular alkene aminooxygenation, which provides methyleneoxy-functionalized disubstituted pyrrolidines and five-membered cyclic ureas from the corresponding γ-alkenyl sulfonamides and N-allylureas, is reported. In addition, some success was achieved in enantioselective desymmetrizations reactions. We discovered that the level of enantioselectivity and diastereoselectivity could be tuned by choice of copper(II) ligands and substrate N ...[more]

PMID: 21841912

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