Microwave-accelerated competing domino processes: a tether-controlled dual pathway into high molecular complexity.
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.
Elkhayat
Zobida
Z
Institut de Chimie des Substances Naturelles, CNRS Gif-sur-Yvette, France.
Safir
Imad
I
Castellote
Isabel
I
Retailleau
Pascal
P
Arseniyadis
Siméon
S
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
D000475:Alkenes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D009942:Organometallic Compounds; D004986:Ether; C013658:propylene; C008261:lead acetate