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Updated: Apr 1, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Formation of the Main Cores Present in Natural Products by Tandem Additions
Kimiaka C Guérard1, Vincent Hamel1, Amandine Guérinot1
1Département de chimie, Université du Québec à Montréal, Laboratoire de Méthodologie et Synthèse de Produits Naturels, C.P.8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec (Canada).
Abstract:
A rapid route to 5,5- and 5,6- bicyclic systems is provided by an 1,3-alkyl-shift process mediated by a hypervalent iodine reagent on aromatics. The structures obtained contain several unsaturations with different behaviors and reactivities. Such diversity allows further elaborations for the rapid formation of compact systems present in a variety of natural products. The potential for further transformations has been demonstrated by performing a double Michael addition. This cyclization process is regio- and stereoselective due to the presence of a former benzylic substituent. Furthermore, an extension of this approach has been accomplished on indole derivatives.
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