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

Autor:	Van Hecke K; Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, North Carolina 28403, United States., Benton TR; Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, North Carolina 28403, United States., Casper M; Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, North Carolina 28403, United States., Mauldin D; Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, North Carolina 28403, United States., Drake B; Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, North Carolina 28403, United States., Morgan JB; Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, North Carolina 28403, United States.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2021 Oct 15; Vol. 23 (20), pp. 7916-7920. Date of Electronic Publication: 2021 Oct 05.
DOI:	10.1021/acs.orglett.1c02914
Abstrakt:	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.
Databáze:	MEDLINE
Externí odkaz:	Zobrazit plný text záznamu