A metathesis-based approach to the synthesis of furans.
The enol ether-olefin ring-closing metathesis reaction has been employed to generate 2,3-dihydrofurans that are equipped with a leaving group. These substrates are at the correct oxidation state to undergo an acid-catalyzed aromatization, and this strategy has been utilized to provide a mild and rapid route (four steps) to a range of novel 2,5-disubstituted furans. [reaction: see text]
Donohoe
Timothy J
TJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, U.K. timothy.donahoe@chem.ox.ac.uk
Fishlock
Lisa P
LP
Lacy
Adam R
AR
Procopiou
Panayiotis A
PA
D000143:Acids / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005663:Furans / Q000138:chemical synthesis*; D008956:Models, Chemical; D010084:Oxidation-Reduction
D000143:Acids; D005663:Furans; C073812:2,3-dihydrofuran