Brønsted Acid Catalyzed Dehydrative Nucleophilic Substitution of C3-Substituted 2-Indolylmethanols with Azlactones

Abstract

An efficient dehydrative nucleophilic substitution reaction of C3-substituted2-indolylmethanols with azlactones has been established. In the whole process, Brønsted acid was supposed to activate two substrates simultaneously. A series of structurally diversified indole derivatives were obtained in generally good yields and high diastereoselectivities (up to 86% yield, >95:5 dr). This protocol not only provides a new strategy for the direct synthesis of structurally diversified indole derivatives, but also enriches the chemistry of 2-indolylmethanols via dehydrative substitution reaction.

Key words

dehydrative nucleophilic substitution - indole derivatives - azlactone - 2-indolylmethanol

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