title: General and highly α-regioselective zinc-mediated prenylation of aldehydes and ketones.
abstract: A simple, efficient, and general α-prenylation approach for the synthesis of a variety of α-prenylated alcohols has been successfully developed. A wide range of α-prenylated alcohol derivatives could be obtained in good yields by highly α-regioselective zinc-mediated prenylation of various aldehydes and ketones with prenyl bromide at 120 °C in HMPA. By simply altering the reaciton solvent and temperature, the method allows the achievement of a highly notable opposite regiocontrol, providing the expected regiochemical product. The method provides a convenient route for the direct α-prenylation of carbonyl compounds in a highly α-regioselective manner using a cheap and convenient mediator. Two possible pathways are proposed to account for the formation of these synthetically difficult-to-obtain molecules.
authors.affiliation: School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, Jiangsu, China. lmzhao@xznu.edu.cn
authors.forename: Li-Ming
authors.initials: LM
authors.lastname: Zhao
authors.forename: Hai-Shan
authors.initials: HS
authors.lastname: Jin
authors.forename: Li-Jing
authors.initials: LJ
authors.lastname: Wan
authors.forename: Li-Ming
authors.initials: LM
authors.lastname: Zhang
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D054876:Prenylation; D013237:Stereoisomerism; D013379:Substrate Specificity; D015032:Zinc / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D007659:Ketones; D015032:Zinc