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Control of diastereoselectivity for iridium-catalyzed allylation of a prochiral nucleophile with a phosphate counterion.

ABSTRACT: We report a highly diastereo- and enantioselective allylation of azlactones catalyzed by the combination of a metallacyclic iridium complex and an optically inactive phosphate anion. The process demonstrates an approach for conducting diastereoselective reactions with prochiral nucleophiles in the presence of metallacyclic allyliridium complexes. The reaction provides access to an array of enantioenriched allylated azlactones containing adjacent tertiary and quaternary carbon centers. Preliminary mechanistic studies suggest that the phosphate and methyl carbonate anions together induce the unusually high diastereoselectivity.

SUBMITTER: Chen W

PROVIDER: S-EPMC3595042 | biostudies-literature | 2013 Feb

REPOSITORIES: biostudies-literature

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Control of diastereoselectivity for iridium-catalyzed allylation of a prochiral nucleophile with a phosphate counterion.

Chen Wenyong W Hartwig John F JF

Journal of the American Chemical Society 20130130 6

We report a highly diastereo- and enantioselective allylation of azlactones catalyzed by the combination of a metallacyclic iridium complex and an optically inactive phosphate anion. The process demonstrates an approach for conducting diastereoselective reactions with prochiral nucleophiles in the presence of metallacyclic allyliridium complexes. The reaction provides access to an array of enantioenriched allylated azlactones containing adjacent tertiary and quaternary carbon centers. Preliminar ...[more]

PMID: 23286279

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