Diastereoselective synthesis of 3-(α-aryl)alkenylindoles from the direct dehydrative coupling of indoles and ketones: A synthetic and theoretical study. Issue 41 (9th October 2020)

• Record Type: Journal Article
• Authors: Barbero, Margherita; Marabello, Domenica; Dughera, Stefano; Sicari, Tiziana; Antenucci, Achille; Ghigo, Giovanni
• Is Part Of: Tetrahedron. Volume 76:Issue 41(2020)
• Publication Date: 2020-10-09
• Subjects: 3-(α-aryl)alkenylindoles -- Diastereoselective reaction -- Dehydrative coupling -- DFT calculations -- Indole functionalisation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131498
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A representative library of 3-(α-aryl)alkenylindoles has been prepared via a Brønsted-acid catalysed dehydrative coupling reaction between alkyl aryl ketones and some indoles. An interesting diastereoselectivity has been observed and has been explained from a mechanistic point of view. Graphical abstract: Image 1 Highlights: 3-(α-Aryl)alkenylindoles are easily prepared via an acid-catalysed direct dehydrative coupling between some ketones and indoles. The observed good diastereoselectivity depending on indole substitution has been explained by a computational method. Alkenylindoles are reactive intermediates, useful for the synthesis of indole-based heterocycles.