title: Microwave-accelerated competing domino processes: a tether-controlled dual pathway into high molecular complexity.
abstract: Bicyclic unsaturated diols undergo a path selective modular domino transformation upon subjection to Pb(OAc)4, the reaction being biased to the nature of the angular substituent. The magnitude of the linking chain and the nature of the angular substituent determine the reaction course. Methylene ether linkage acts as an autoremovable directing group (ring-retained domino product 5), whereas a propylene linkage switches the path toward the ring-expanded type 21 domino product. Reaction times were substantially reduced using microwave irradiation.
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS Gif-sur-Yvette, France.
authors.forename: Zobida
authors.initials: Z
authors.lastname: Elkhayat
authors.forename: Imad
authors.initials: I
authors.lastname: Safir
authors.forename: Isabel
authors.initials: I
authors.lastname: Castellote
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Siméon
authors.initials: S
authors.lastname: Arseniyadis
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D004986:Ether / Q000737:chemistry*; D008872:Microwaves; D009942:Organometallic Compounds / Q000737:chemistry; D013997:Time Factors
chemical_list: D000475:Alkenes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D009942:Organometallic Compounds; D004986:Ether; C013658:propylene; C008261:lead acetate