Synthesis of Spiroindenes via Palladium Catalysis Using Oxabicycles as Acetylene Surrogates
We report the palladium-catalyzed synthesis of spiroindenes using oxabicycles as acetylene surrogates. This protocol allows for the synthesis of a diverse library of heterocyclic-tethered spiroindenes. Preliminary results using enantioenriched oxabicycles as chiral auxiliaries allow for the synthesis of enantioenriched spiroindenes. The formation of unusual 6-<i>endo</i>-<i>trig</i> naphthyl side products is observed for substrates with proximal Lewis basic nitrogens.
Authors
- Xavier Abel‐Snape (ORCID: https://orcid.org/0000-0003-3785-7617)
- Mark Lautens (ORCID: https://orcid.org/0000-0002-0179-2914)
- Clara Jans (ORCID: https://orcid.org/0009-0007-2446-2778)
- Lorenzo Rizzo (ORCID: https://orcid.org/0009-0000-3288-3635)
- Gregory Hughes (ORCID: https://orcid.org/0000-0003-2333-5797)
- Armaan Grewal
Institutions
- Merck & Co., Inc., Rahway, NJ, USA (United States) (US)
- University of Toronto (CA)
- Davenport University (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-11-26
- DOI
- https://doi.org/10.1021/acs.orglett.5c04430
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00