Chemoselective Double Allylic Substitutions with Carbon Nucleophiles: Access to Tetrahydroindoles and Tetrahydrocarbazoles
A chemoselective double allylic substitution involving two different carbon nucleophiles is described. The reaction relies on a dual catalytic approach, with a Lewis acid promoting the first allylic substitution and Pd promoting the second step. Starting from simple allylic diols, a diversity of polycyclic structures can be obtained, including tetrahydroindole, tetrahydrocarbazole, and tetrahydronaphthalene.
Authors
- Aurélien de la Torre (ORCID: https://orcid.org/0000-0002-7909-0234)
- Cyrille Kouklovsky (ORCID: https://orcid.org/0000-0001-5399-9469)
- Sébastien Prévost (ORCID: https://orcid.org/0000-0001-5518-1679)
- Lucas Pagès (ORCID: https://orcid.org/0009-0000-0146-5342)
- Bocheng Chen (ORCID: https://orcid.org/0009-0001-0471-7063)
Institutions
- Centre National de la Recherche Scientifique (FR)
- École Polytechnique (FR)
- École Nationale Supérieure de Techniques Avancées (FR)
- Université Paris-Saclay (FR)
- Laboratoire de Synthèse Organique (FR)
- Institut de Chimie Moléculaire et des Matériaux d'Orsay (FR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-22
- DOI
- https://doi.org/10.1021/acs.joc.5c00121
- Citations
- 1
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Labex
- China Scholarship Council
- Centre National de la Recherche Scientifique
- Université Paris-Saclay