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Updated: Aug 31, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl
1Department of Organic and Medicinal Chemistry, Wrocław University of Technology, Wyb. Wyspiańskiego 26, Wrocław 50-370, Poland.
Abstract:
The unexpected domino coupling and rearrangement of the Cinchona alkaloid skeleton has been found to occur in the reaction of 9-chloro-9-deoxy-alkaloids with Grignards from peri-dihalogenonaphthalene. The cyclization and migration of the central quinuclidinylmethyl group (C9) from position C-4' to position C-3' of quinoline formed a novel chiral ring system of 5-aza-7H-benzo[no]tetraphene, yielding products of unlike configuration. The proposed reaction pathway involves radical intermediates.
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