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. 2008 Jul 3;10(13):2721-4.
doi: 10.1021/ol8008792. Epub 2008 Jun 4.

Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction

Ana Minatti  1 , Stephen L Buchwald
Affiliations

Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction

Ana Minatti et al. Org Lett. .

Abstract

A highly efficient one-pot procedure for the synthesis of indolines and their homologues based on a domino Cu-catalyzed amidation/nucleophilic substitution reaction has been developed. Substituted 2-iodophenethyl mesylates and related compounds afforded the corresponding products in excellent yields. No erosion of optical purity was observed when transforming enantiomerically pure mesylates under the reaction conditions.

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Figures

Scheme 1
Scheme 1
Known and Envisioned Strategies for the Synthesis of Indolines
Scheme 2
Scheme 2. Possible Mechanistic Pathways
A, A′: intermolecular Cu-cat. amidation and hydroamidation. B, B′: intermolecular Cu-cat. or uncat. amidation and intramolecular Cu-cat. amidation. C, C′: intermolecular Cu-cat. amidation and SN2 reaction.
Scheme 3
Scheme 3
Experiments Conducted to Elucidate the Reaction Mechanism
See this image and copyright information in PMC

References

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