Open AccessPalladium-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) - enantioselective synthesis , desymmetrization , chemistry , aziridine , palladium , catalysis , tryptamine , yield (engineering) , indole test , amine gas treating , combinatorial chemistry , organic chemistry , stereochemistry , ring (chemistry) , biochemistry , materials science , metallurgy
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.