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Enantioselective carbocycle formation through intramolecular Pd-catalyzed allyl-aryl cross-coupling.

ABSTRACT: Aryl electrophiles containing tethered allylboronate units undergo efficient intramolecular coupling in the presence of a chiral palladium catalyst to give enantioenriched carbocyclic products. The reaction is found to be quite general, affording 5, 6, and 7-membered carbocyclic products as single regioisomers and with moderate enantioselectivities. Examination of differential coupling partners points to rapid allyl-equilibration as a key stereodefining feature.

SUBMITTER: Schuster CH

PROVIDER: S-EPMC4156259 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Enantioselective carbocycle formation through intramolecular Pd-catalyzed allyl-aryl cross-coupling.

Schuster Christopher H CH Coombs John R JR Kasun Zachary A ZA Morken James P JP

Organic letters 20140808 17

Aryl electrophiles containing tethered allylboronate units undergo efficient intramolecular coupling in the presence of a chiral palladium catalyst to give enantioenriched carbocyclic products. The reaction is found to be quite general, affording 5, 6, and 7-membered carbocyclic products as single regioisomers and with moderate enantioselectivities. Examination of differential coupling partners points to rapid allyl-equilibration as a key stereodefining feature. ...[more]

PMID: 25105510

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