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The diastereoselective synthesis of pyrroloindolines by Pd-catalyzed dearomative cycloaddition of 1-tosyl-2-vinylaziridine to 3-nitroindoles

Rivinoja, DJ, Gee, YS, Gardiner, MG ORCID: 0000-0001-6373-4253, Ryan, JH and Hyland, CJT 2017 , 'The diastereoselective synthesis of pyrroloindolines by Pd-catalyzed dearomative cycloaddition of 1-tosyl-2-vinylaziridine to 3-nitroindoles' , ACS Catalysis, vol. 7, no. 2 , pp. 1053-1056 , doi: 10.1021/acscatal.6b03248.

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Abstract

An efficient, diastereoselective synthesis of densely functionalized pyrroloindolines is reported. The reaction proceeds via cycloaddition of a vinylaziridine-derived Pd-stabilized 1,3-dipole to electron-deficient 3-nitroindoles. The reactions give the trans diastereoisomer with high selectivity; however, when a 4-substituent is present on the indole ring, a reversal of diastereoselectivity is observed.

Item Type: Article
Authors/Creators:Rivinoja, DJ and Gee, YS and Gardiner, MG and Ryan, JH and Hyland, CJT
Keywords: pyrroloindolines, palladium catalysis, dearomatization, indoles, [3 + 2] cycloaddition, vinylaziridines
Journal or Publication Title: ACS Catalysis
Publisher: AMER CHEMICAL SOC
ISSN: 2155-5435
DOI / ID Number: 10.1021/acscatal.6b03248
Copyright Information:

© 2016 American Chemical Society

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