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

[Image: see text] 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 the...

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Detalles Bibliográficos
Autores principales: Linne, Yannick, Lohrberg, Daniel, Struwe, Henry, Linne, Elvira, Stohwasser, Anastasia, Kalesse, Markus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476192/
https://www.ncbi.nlm.nih.gov/pubmed/37594929
http://dx.doi.org/10.1021/acs.joc.3c01309
Descripción
Sumario:[Image: see text] 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.