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Palladium-Catalyzed, Enantioselective Desymmetrization of N-Acylaziridines with Indoles.

ABSTRACT: Ring opening reactions of meso-aziridines generate chiral amine derivatives where the control of stereochemistry is possible through enantioselective catalysis. We report the use of a diphosphine-palladium(II) catalyst for the highly enantioselective desymmetrization of N-acylaziridines with indoles. The β-tryptamine products are isolated in moderate to high yield across a range of indole and aziridine substitution patterns. The synthetic utility of β-tryptamine products is demonstrated by conversion to the brominated pyrroloindoline derivative.

SUBMITTER: Van Hecke K

PROVIDER: S-EPMC9022218 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed, Enantioselective Desymmetrization of N-Acylaziridines with Indoles.

Van Hecke Kinney K Benton Tyler R TR Casper Michael M Mauldin Dustin D Drake Brandon B Morgan Jeremy B JB

Organic letters 20211005 20

Ring opening reactions of meso-aziridines generate chiral amine derivatives where the control of stereochemistry is possible through enantioselective catalysis. We report the use of a diphosphine-palladium(II) catalyst for the highly enantioselective desymmetrization of N-acylaziridines with indoles. The β-tryptamine products are isolated in moderate to high yield across a range of indole and aziridine substitution patterns. The synthetic utility of β-tryptamine products is demonst ...[more]

PMID: 34609884

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