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Diastereoselective construction of functionalized homoallylic alcohols by Ni-catalyzed diboron-promoted coupling of dienes and aldehydes.

ABSTRACT: The nickel-catalyzed reaction of carbonyls and dienes was accomplished in a regio- and stereoselective fashion employing a stoichiometric amount of bis(pinacolato)diboron. This reductive coupling furnishes an allyl boronic ester as the reaction product, a compound which was readily converted to the derived allylic alcohol by oxidative workup.

SUBMITTER: Cho HY

PROVIDER: S-EPMC2676113 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Diastereoselective construction of functionalized homoallylic alcohols by Ni-catalyzed diboron-promoted coupling of dienes and aldehydes.

Cho Hee Yeon HY Morken James P JP

Journal of the American Chemical Society 20081201 48

The nickel-catalyzed reaction of carbonyls and dienes was accomplished in a regio- and stereoselective fashion employing a stoichiometric amount of bis(pinacolato)diboron. This reductive coupling furnishes an allyl boronic ester as the reaction product, a compound which was readily converted to the derived allylic alcohol by oxidative workup. ...[more]

PMID: 18998642

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