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Iron-catalyzed aminohydroxylation of olefins.

ABSTRACT: We have discovered that N-sulfonyl oxaziridines react with a broad range of olefins in the presence of iron salts to afford 1,3-oxazolidines. This process provides access to 1,2-aminoalcohols with the opposite sense of regioselectivity produced from the copper-catalyzed oxyamination previously reported by our laboratories. Thus, either regioisomeric form of 1,2-aminoalcohols can easily be obtained from the reaction of oxaziridines with olefins, and the sense of regioselectivity can be controlled by the appropriate choice of inexpensive, nontoxic, first-row transition-metal catalyst.

SUBMITTER: Williamson KS

PROVIDER: S-EPMC2857537 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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Iron-catalyzed aminohydroxylation of olefins.

Williamson Kevin S KS Yoon Tehshik P TP

Journal of the American Chemical Society 20100401 13

We have discovered that N-sulfonyl oxaziridines react with a broad range of olefins in the presence of iron salts to afford 1,3-oxazolidines. This process provides access to 1,2-aminoalcohols with the opposite sense of regioselectivity produced from the copper-catalyzed oxyamination previously reported by our laboratories. Thus, either regioisomeric form of 1,2-aminoalcohols can easily be obtained from the reaction of oxaziridines with olefins, and the sense of regioselectivity can be controlled ...[more]

PMID: 20232850

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