title: 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 β-hydride elimination at the allylic position.
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
authors.forename: Ryan J
authors.initials: RJ
authors.lastname: DeLuca
authors.forename: Matthew S
authors.initials: MS
authors.lastname: Sigman
mesh_terms: D000478:Alkylation; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D020005:Propanols; C006463:allyl alcohol; D010165:Palladium