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Peer-reviewedCC BY-NC-ND 4.0JACS Au

Intramolecular Stereospecific Skeletal Rearrangement via Nonclassical Carbocations

  • Kaushalendra Patel1
  • Belal Awwad1
  • Ilan Marek1
  1. 1Technion−Israel Institute of Technology , , ,
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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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Cite

BibTeXRIS
BibTeX
@article{patel2026intramolecular,
  title = {{Intramolecular Stereospecific Skeletal Rearrangement via Nonclassical Carbocations}},
  author = {Kaushalendra Patel and Belal Awwad and Ilan Marek},
  journal = {JACS Au},
  year = {2026},
  month = oct,
  doi = {10.1021/jacsau.6c00439},
  url = {https://pubs.acs.org/jaaucr/article/6/10/5571/5448615/Intramolecular-Stereospecific-Skeletal},
  note = {CC BY-NC-ND 4.0},
}
RIS
TY  - JOUR
TI  - Intramolecular Stereospecific Skeletal Rearrangement via Nonclassical Carbocations
AU  - Kaushalendra Patel
AU  - Belal Awwad
AU  - Ilan Marek
PY  - 2026
DA  - 2026/10/11
JO  - JACS Au
DO  - 10.1021/jacsau.6c00439
UR  - https://pubs.acs.org/jaaucr/article/6/10/5571/5448615/Intramolecular-Stereospecific-Skeletal
AB  - 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.
SN  - 2691-3704
ER  -