Enantioselective Synthesis of Tertiary Alcohols through a Zirconium-Catalized Friedel-Crafts Alkylation of Pyrroles with alpha-Ketoesters

Chiral complexes of 1,10-bi-2-naphthol-based ligands with zirconium tert-butoxide catalyze the Friedel Crafts alkylation of pyrroles with R-ketoesters to afford tertiary alcohols in good yields and ee up to 98%. The reaction is also of application to 4,7-dihydroindole to give C2-alkylated indoles after oxidation with p-benzoquinone.We thank the Ministerio de Ciencia e Innovacion and FEDER (Grant CTQ2009-13083) and the Generalitat Valenciana (Grant ACOMP/2011/267) for financial support. C.V. thanks the Generalitat Valenciana for a predoctoral grant.Blay, G.; Fernández, I.; Muñoz Roca, MDC.; Pedro, J.; Recuenco, A.; Vila, C. (2011). Enantioselective Synthesis of Tertiary Alcohols through a Zirconium-Catalized Friedel-Crafts Alkylation of Pyrroles with alpha-Ketoesters. Journal of Organic Chemistry. 76:6286-6294. doi:10.1021/jo2010704S628662947