Palladium-Catalyzed, Enantioselective Desymmetrization of N-Acylaziridines with Indoles | Zendy

Kinney Van Hecke | Zendy; Tyler R. Benton | Zendy; Michael Casper | Zendy; Dustin Mauldin | Zendy; Brandon Drake | Zendy; Jeremy B. Morgan | Zendy

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

Author(s) -

Kinney Van Hecke,

Tyler R. Benton,

Michael Casper,

Dustin Mauldin,

Brandon Drake,

Jeremy B. Morgan

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c02914

Subject(s) - desymmetrization , chemistry , enantioselective synthesis , palladium , catalysis , stereochemistry , organic chemistry , combinatorial chemistry

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.

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