Synthesis of halogenated bicyclic molecules involving Prins cyclization from aldehydes and non-conjugated diene alcohol

  1. Kouichi MatsumotoORCID Logo,
  2. Keisuke Ohtsuka,
  3. Naruto Hasebe,
  4. Kota Terada,
  5. Masahiko Maekawa,
  6. Yoshihide Nakao,
  7. Keiji NishiwakiORCID Logo and
  8. Hideo AndoORCID Logo

Submitting author affiliation: Kindai University, Osaka, Japan

Beilstein Arch. 2021, 202138. https://doi.org/10.3762/bxiv.2021.38.v1

Published 21 May 2021

  • Preprint

Abstract

The reactions of aldehydes and a non-conjugated alcohol, (E)-octa-3,7-dien-1-ol, in the presence of halogen-containing reagents afforded the corresponding halogenated bicyclic molecules in good yields. The optimization, scope and limitations of the reactions as well as scale-up reactions have been examined. Quantum chemical calculations helped clarify the microscopic mechanism of a key reaction process, the introduction of a Cl atom to a bicyclic carbocation.

Keywords: Prins Cyclization; C-C Bond Formation; Bicyclic Molecules; Sequential Reactions

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Matsumoto, K.; Ohtsuka, K.; Hasebe, N.; Terada, K.; Maekawa, M.; Nakao, Y.; Nishiwaki, K.; Ando, H. Beilstein Arch. 2021, 202138. doi:10.3762/bxiv.2021.38.v1

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