1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols

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Authors

  • Yannick Linne
  • Daniel Lohrberg
  • Henry Struwe
  • Elvira Linne
  • Anastasia Stohwasser
  • Markus Kalesse

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Original languageEnglish
Pages (from-to)12623–12629
Number of pages7
JournalJournal of Organic Chemistry
Volume88
Issue number17
Early online date18 Aug 2023
Publication statusPublished - 1 Sept 2023

Abstract

The development of new methods and protocols for the synthesis of biologically active substances remains one of the most important pillars in organic chemistry, and one of these privileged structural motifs are allylic alcohols. The method of choice to date for the synthesis of these is the Nozaki-Hiyama-Takai-Kishi reaction. We describe here a valuable alternative to the synthesis of allylic alcohols via 1,2-metallate rearrangement. In this work, various vinyl boronic esters with different functional groups have been applied in the Hoppe-Matteson-Aggarwal reaction. In addition, two monoterpenoids were constructed via this convergent synthetic strategy.

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Cite this

1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols. / Linne, Yannick; Lohrberg, Daniel; Struwe, Henry et al.
In: Journal of Organic Chemistry, Vol. 88, No. 17, 01.09.2023, p. 12623–12629.

Research output: Contribution to journalArticleResearchpeer review

Linne, Y, Lohrberg, D, Struwe, H, Linne, E, Stohwasser, A & Kalesse, M 2023, '1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols', Journal of Organic Chemistry, vol. 88, no. 17, pp. 12623–12629. https://doi.org/10.1021/acs.joc.3c01309
Linne Y, Lohrberg D, Struwe H, Linne E, Stohwasser A, Kalesse M. 1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols. Journal of Organic Chemistry. 2023 Sept 1;88(17):12623–12629. Epub 2023 Aug 18. doi: 10.1021/acs.joc.3c01309
Linne, Yannick ; Lohrberg, Daniel ; Struwe, Henry et al. / 1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols. In: Journal of Organic Chemistry. 2023 ; Vol. 88, No. 17. pp. 12623–12629.
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