Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans |
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| Authors: | Huseyin Erguven Cuihan Zhou Bruce A Arndtsen |
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| Institution: | Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal QC H3A0B8 Canada.; Department of Chemistry and Chemical Biology, Rutgers University, 123 Bevier Road, Piscataway, NJ 08854 USA |
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| Abstract: | A new class of phosphorus-containing 1,3-dipoles can be generated by the multicomponent reaction of aldehydes, acid chlorides and the phosphonite PhP(catechyl). These 1,3-dipoles are formally cyclic tautomers of simple Wittig-type ylides, where the angle strain and moderate nucleophilicity in the catechyl-phosphonite favor their cyclization and also direct 1,3-dipolar cycloaddition to afford single regioisomers of substituted products. Coupling the generation of the dipoles with 1,3-dipolar cycloaddition offers a unique, modular route to furans from combinations of available aldehydes, acid chlorides and alkynes with independent control of all four substituents.A new class of phosphorus-containing 1,3-dipoles has been developed, which, when coupled with cycloaddition, offers modular synthesis of furans with independent control of all four substituents. |
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