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A one-pot access to cycloalkano[1,2-a]indoles through an intramolecular alkyl migration reaction in indolylborates
Authors:Minoru Ishikura  Wataru Ida
Affiliation:a Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan
b Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagatoge-Cho, Hirakata, Osaka 573-0101, Japan
Abstract:A novel one-pot protocol for the preparation of cycloalkano[1,2-a]indoles by way of an intramolecular alkyl migration reaction in cyclic indolylborates is described. NaOMe was found to act as a successful trialkylboryl-protecting group against to the lithiation at the C2 of the indole ring. Treatment of cyclic indolylborates with electrophiles produced cycloalkano-[1,2-a]indoles.
Keywords:Cyclic indolylborate   Hydroboration   Intramolecular alkyl migration   [a]-Annelated indoles
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