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- Title
Nickel(II)-Catalyzed Formal [3+2] Cycloadditions between Indoles and Donor–Acceptor Cyclopropanes.
- Authors
Quezada, Víctor; Castroagudín, Mariña; Verdugo, Felipe; Ortiz, Sergio; Zaragoza, Guillermo; Nachtigall, Fabiane M.; Reis, Francisco A. A.; Castro-Alvarez, Alejandro; Santos, Leonardo S.; Nelson, Ronald
- Abstract
This article describes the development of a nickel-catalyzed regio- and diastereoselective formal [3+2] cycloaddition between N-substituted indoles and donor–acceptor cyclopropanes to synthesize cyclopenta[b]indoles. Optimized reaction conditions provide the desired nitrogen-containing cycloadducts in up to 93% yield and dr 8.6:1 with complete regioselectivity. The substrate scope showed high tolerance to various substituted indoles and cyclopropanes, resulting in the synthesis of six new cyclopenta[b]indoles and the isolation of five derivatives previously reported in the literature. In addition, a mechanistic proposal for the reaction was studied through online reaction monitoring by ESI-MS, allowing for the identification of the reactive intermediates in the Ni(II) catalyzed process. X-ray crystallography confirmed the structure and relative endo stereochemistry of the products. This method enables the fast and efficient construction of fused indolines from readily accessible starting materials.
- Subjects
INDOLE; INDOLE compounds; CYCLOPROPANE derivatives; X-ray crystallography; NICKEL; STEREOCHEMISTRY
- Publication
Molecules, 2024, Vol 29, Issue 7, p1604
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules29071604