Dearomative Amination Cyclization of Tryptamines and Tryptophols via Enantioselective 1,6‐Addition of p‐Quinone Diimides (p‐QDIs)

A chiral phosphoric acid catalyzed enantioselective aminative dearomatization cyclization of tryptamines and tryptophols, which enables the rapid access of 3-amino-pyrroloindoline and 3-amino-furoindoline derivatives with excellent enantioselectivities.

Abstract

A method utilizing p-quinone diimides (p-QDIs) as electrophilic nitrogen source to facilitate a highly enantioselective dearomative cyclization of tryptamine and tryptophol derivatives has been developed. This approach which proceeds via a 1,6-addition of p-QDIs enables the rapid and efficient synthesis of chiral 3-amino-pyrroloindoline and 3-amino-furoindolines derivatives with excellent stereochemical control (up to 99%). Development of an alternate one-pot method, coupled with some synthetic transformations further elevates the practical utility of this strategy.

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