4.7 Article

Enantioselective Synthesis of Tertiary Alcohols through a Zirconium-Catalyzed Friedel-Crafts Alkylation of Pyrroles with α-Ketoesters

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 15, Pages 6286-6294

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo2010704

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Funding

  1. Ministerio de Ciencia e Innovacion
  2. FEDER [CTQ2009-13083]
  3. Generalitat Valenciana [ACOMP/2011/267]

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Chiral complexes of 1,1'-bi-2-naphthol-based ligands with zirconium tert-butoxide catalyze the Friedel Crafts alkylation of pyrroles with alpha-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.

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