Anionic halocuprate(II) complexes as catalysts for the oxaziridine-mediated aminohydroxylation of olefins.

ABSTRACT: We have discovered that the oxaziridine-mediated copper-catalyzed aminohydroxylation reaction recently discovered in our laboratories is dramatically accelerated in the presence of halide additives. The use of this more active catalyst system enables the efficient aminohydroxylation of electronically and sterically deactivated styrenes and also enables the use of nonstereogenic 3,3-dialkyl oxaziridines as terminal oxidants in the aminohydroxylation reaction. We present evidence that anionic halocuprate(II) complexes are the catalytically active species responsible for the increased reactivity under these conditions. This unexpected observation has led us to re-evaluate our mechanistic understanding of this reaction. On the basis of the results of a variety of radical trapping experiments,

SUBMITTER: Benkovics T 

PROVIDER: S-EPMC2743488 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature