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JOURNALS // Uspekhi Khimii // Archive

Usp. Khim., 2022 Volume 91, Issue 8, Pages 1–95 (Mi rcr4397)

This article is cited in 2 papers

[3,3]-Sigmatropic rearrangements: a variety of methods and recent advances

V. D. Dyachenko, B. N. Baryshev, V. G. Nenajdenko

Lomonosov Moscow State University, Faculty of Chemistry

Abstract: The systematic review integrates and analyzes data on [3,3]-sigmatropic rearrangements published in the past decade. The main types of [3,3]-sigmatropic rearrangements are highlighted, optimal catalytic systems for various types of transformations and for various classes of compounds are considered. Examples are given for the use of such reactions in the synthesis of structurally complex, biologically active, natural and practically valuable compounds. For a number of processes, general mechanistic features of their behaviour, the geometry of transition states and the structures of inermediates are discussed.
The bibliography includes 533 references.

Keywords: [3,3]-sigmatropic rearrangements, tandem reactions, Claisen rearrangement, Johnson-Claisen rearrangement, Eschenmoser-Claisen rearrangement, Ireland-Claisen rearrangement, transition metal catalysis.

Received: 16.11.2021

DOI: 10.1070/RCR5039


 English version:
Russian Chemical Reviews, 2022, 91:8, 1–96

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© Steklov Math. Inst. of RAS, 2024