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

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.

SUBMITTER: Linne Y

PROVIDER: S-EPMC10476192 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature

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

Linne Yannick Y Lohrberg Daniel D Struwe Henry H Linne Elvira E Stohwasser Anastasia A Kalesse Markus M

The Journal of organic chemistry 20230818 17

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 func ...[more]

PMID: 37594929

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