Intramolecular Stereospecific Skeletal Rearrangement via Nonclassical Carbocations
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Updated: Oct 31, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Kaushalendra Patel1, Belal Awwad1, Ilan Marek1
1Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis, Technion-Israel Institute of Technology, Haifa 3200009, Israel.
Abstract:
A stereospecific, Lewis acid-catalyzed intramolecular nucleophilic substitution at fully substituted carbon stereocenters is described, proceeding through nonclassical cyclopropyl carbinyl (CPC) carbocation intermediates and complete skeletal rearrangement. The method displays excellent regio- and diastereoselectivity, offering a general strategy for exploiting nonclassical carbocations in stereoselective synthesis.
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