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

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Linne, Y.; Lohrberg, D.; Struwe, H.; Linne, E.; Stohwasser, A. et al.: 1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols. In: The Journal of Organic Chemistry 88 (2023), Nr. 17, S. 12623-12629. DOI: https://doi.org/10.1021/acs.joc.3c01309

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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.
License of this version: CC BY 4.0 Unported
Document Type: Article
Publishing status: publishedVersion
Issue Date: 2023
Appears in Collections:Naturwissenschaftliche Fakultät

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1 image of flag of Germany Germany 17 58.62%
2 image of flag of United States United States 5 17.24%
3 image of flag of Israel Israel 4 13.79%
4 image of flag of Sweden Sweden 1 3.45%
5 image of flag of Japan Japan 1 3.45%
6 image of flag of Spain Spain 1 3.45%

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