Issue 42, 2022

Recent advances in metal-catalysed asymmetric sigmatropic rearrangements

Abstract

Asymmetric sigmatropic rearrangement is a powerful organic transformation via substrate-reorganization to efficiently increase molecular complexity from readily accessible starting materials. In particular, a high level of diastereo- and enantioselectivity can be readily accessed through well-defined and predictable transition states in [3,3], [2,3]-sigmatropic rearrangements, which have been widely applied in the synthesis of various chiral building blocks, natural products, and pharmaceuticals. In recent years, catalytic asymmetric sigmatropic rearrangements involving chiral metal complexes to induce stereocontrol have been intensively studied. This review presents an overview of metal-catalysed enantioselective versions of sigmatropic rearrangements in the past two decades, mainly focusing on [3,3], [2,3], and [1,3]-rearrangements, to show the development of substrate design, new catalyst exploitation, and novel cascade processes. In addition, their application in the asymmetric synthesis of complex natural products is also exemplified.

Graphical abstract: Recent advances in metal-catalysed asymmetric sigmatropic rearrangements

Article information

Article type
Review Article
Submitted
08 iyl 2022
Accepted
22 sen 2022
First published
23 sen 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 12290-12308

Recent advances in metal-catalysed asymmetric sigmatropic rearrangements

Y. Liu, X. Liu and X. Feng, Chem. Sci., 2022, 13, 12290 DOI: 10.1039/D2SC03806D

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