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

Citation

Rivinoja, DJ and Gee, YS and Gardiner, MG and Ryan, JH and Hyland, CJT, The diastereoselective synthesis of pyrroloindolines by Pd-catalyzed dearomative cycloaddition of 1-tosyl-2-vinylaziridine to 3-nitroindoles, ACS Catalysis, 7, (2) pp. 1053-1056. ISSN 2155-5435 (2017) [Refereed Article]

Copyright Statement

2016 American Chemical Society

DOI: doi:10.1021/acscatal.6b03248

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 Details

Item Type:Refereed Article
Keywords:pyrroloindolines, palladium catalysis, dearomatization, indoles, [3 + 2] cycloaddition, vinylaziridines
Research Division:Chemical Sciences
Research Group:Inorganic Chemistry
Research Field:Transition Metal Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Gardiner, MG (Associate Professor Michael Gardiner)
ID Code:122792
Year Published:2017
Web of Science® Times Cited:21
Deposited By:Chemistry
Deposited On:2017-11-29
Last Modified:2018-03-29
Downloads:0

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