title: One-pot organocatalytic domino Michael-aldol and intramolecular SN2 reactions. Asymmetric synthesis of highly functionalized epoxycyclohexanone derivatives.
abstract: The development of the organocatalytic asymmetric one-pot Michael-Darzens condensation giving highly functionalized complex epoxycyclohexanone derivatives with up to four chiral centers is presented. Depending on the reaction conditions, either the polysubstituted 7-oxa-bicyclo[4.1.0]heptan-2-one ring system or 2-chloro-cyclohex-2-enone derivatives can be formed. For the former class of compounds a high diversity in substitution pattern is demonstrated, and the optically active products are obtained in excellent diastereo- and enantioselectivities. The potential synthetic applications of the products have been demonstrated by performing a series of highly diastereoselective transformations leading to optically active products useful for the life-science industry. Furthermore, mechanistic investigations on the formation of the chiral centers in the optically active epoxycyclohexanone are presented.
authors.affiliation: The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.
authors.forename: Mauro
authors.initials: M
authors.lastname: Marigo
authors.forename: Søren
authors.initials: S
authors.lastname: Bertelsen
authors.forename: Aitor
authors.initials: A
authors.lastname: Landa
authors.forename: Karl Anker
authors.initials: KA
authors.lastname: Jørgensen