title: Unusual regioselectivity in the opening of epoxides by carboxylic acid enediolates.
abstract: Addition of carboxylic acid dianions appears to be a potential alternative to the use of aluminium enolates for nucleophilic ring opening of epoxides. These conditions require the use of a sub-stoichiometric amount of amine (10% mol) for dianion generation and the previous activation of the epoxide with LiCl. Yields are good, with high regioselectivity, but the use of styrene oxide led, unexpectedly, to a mixture resulting from the attack on both the primary and secondary carbon atoms. Generally, a low diastereoselectivity is seen on attack at the primary center, however only one diastereoisomer was obtained from attack to the secondary carbon of the styrene oxide.
authors.affiliation: Department of Organic Chemistry, Universitat de València, Dr. Moliner 50, 46100 Burjassot, Spain.
authors.forename: Luis R
authors.initials: LR
authors.lastname: Domingo
authors.forename: Salvador
authors.initials: S
authors.lastname: Gil
authors.forename: Margarita
authors.initials: M
authors.lastname: Parra
authors.forename: José
authors.initials: J
authors.lastname: Segura
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D004852:Epoxy Compounds; C013690:styrene oxide