RESUMO
An efficient and attractive synthesis of a series of novel poly-functionalized phosphorus zwitterions was achieved via three-component reactions of the corresponding functional nucleophiles, aldehydes, and Bu(3)P in the presence of acidic promoter. These polysubstituted zwitterions could regioselectively undergo further transformations to synthetically important furanonaphthoquinones and related products via the intramolecular Wittig reaction. These methods could have potential application in synthetic and pharmaceutical chemistry for its facilitation and easily accessible commercial materials.
Assuntos
Furanos/síntese química , Naftoquinonas/síntese química , Furanos/química , Íons/química , Naftoquinonas/química , Fósforo/química , EstereoisomerismoRESUMO
An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,ß-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus ylides in the intramolecular Wittig reactions, and their mechanisms were also investigated by DFT calculations.