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Enantioselective Synthesis of 3,3-Disubstituted-2,3-dihydrobenzofurans by Intramolecular
Luiz Paulo Melchior de Oliveira Leão1, Otto Daolio Köster1, Leonardo José Duarte2
1Chemistry Institute, State University of Campinas, Unicamp, 13083-970 Campinas, São Paulo, Brazil.
Abstract:
The enantioselective one-pot synthesis of 3,3-disubstituted-2,3-dihydrobenzofuran was developed via a strategy involving a palladium-catalyzed Heck-Matsuda reaction, followed by subsequent carbonylation and/or an organotin transmetalation step employing chiral N,N ligands. The one-pot reaction requires mild conditions and tolerates a wide range of functional groups. This method provides straightforward access to a diverse array of enantioenriched dihydrobenzofurans bearing a ketone or an alkyl side chain adjacent to the generated quaternary stereogenic center in yields up to 91% and er up to 99:1.
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