title: One-step synthesis of 1-chloro-3-arylacetone derivatives from arylacetic acids.
abstract: A practical one-step method has been developed to prepare α-chloroketones from readily available, inexpensive phenylacetic acid derivatives. The method utilizes the unique reactivity of an intermediate Mg-enolate dianion, which displays selectivity for the carbonyl carbon of chloromethyl carbonyl electrophiles. Decarboxylation of the intermediate occurs spontaneously during the reaction quench. The utility of the reaction products has been demonstrated through the total synthesis of the natural product cimiracemate B.
authors.affiliation: Department of Process Research, Merck Research Laboratory , Rahway, New Jersey 07065, United States.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Zacuto
authors.forename: Robert F
authors.initials: RF
authors.lastname: Dunn
authors.forename: Margaret
authors.initials: M
authors.lastname: Figus
mesh_terms: D000096:Acetone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D010648:Phenylacetates / Q000737:chemistry*; D010666:Phenylpropionates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D010648:Phenylacetates; D010666:Phenylpropionates; D000096:Acetone; C499963:cimiracemate B; C008863:1-phenyl-2-propanone