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Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester.

ABSTRACT: An aryl substrate with dual functionality consisting of a nitrile oxide and a pinacolyl boronate ester was prepared by mild hypervalent iodine oxidation (diacetoxyiodobenzene) of the corresponding aldoxime, without decomposition of the boronate functionality. The nitrile oxide was trapped in situ with a variety of dipolarophiles to yield aryl isoxazolines with the boronate ester function intact and available for subsequent reaction.

SUBMITTER: Harding SL

PROVIDER: S-EPMC3343286 | biostudies-other | 2012

REPOSITORIES: biostudies-other

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Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester.

Harding Sarah L SL Marcuccio Sebastian M SM Savage G Paul GP

Beilstein journal of organic chemistry 20120419

An aryl substrate with dual functionality consisting of a nitrile oxide and a pinacolyl boronate ester was prepared by mild hypervalent iodine oxidation (diacetoxyiodobenzene) of the corresponding aldoxime, without decomposition of the boronate functionality. The nitrile oxide was trapped in situ with a variety of dipolarophiles to yield aryl isoxazolines with the boronate ester function intact and available for subsequent reaction. ...[more]

PMID: 22563358

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