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The palladium-catalyzed anti-Markovnikov hydroalkylation of allylic alcohol derivatives.

ABSTRACT: A palladium-catalyzed hydroalkylation reaction of protected allylic alcohols using alkylzinc bromide reagents is reported. This account includes numerous allylic, homoallylic, and bishomoallylic alcohol derivatives, all with a uniform selectivity of >20:1 for the anti-Markovnikov product. The reaction features the ability to deliver enantiomerically enriched alcohols in unfunctionalized regions, which results from the catalyst avoiding ?-hydride elimination at the allylic position.

SUBMITTER: DeLuca RJ

PROVIDER: S-EPMC3539300 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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The palladium-catalyzed anti-Markovnikov hydroalkylation of allylic alcohol derivatives.

DeLuca Ryan J RJ Sigman Matthew S MS

Organic letters 20121219 1

A palladium-catalyzed hydroalkylation reaction of protected allylic alcohols using alkylzinc bromide reagents is reported. This account includes numerous allylic, homoallylic, and bishomoallylic alcohol derivatives, all with a uniform selectivity of >20:1 for the anti-Markovnikov product. The reaction features the ability to deliver enantiomerically enriched alcohols in unfunctionalized regions, which results from the catalyst avoiding β-hydride elimination at the allylic position. ...[more]

PMID: 23252845

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