4.6 Review

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

Journal

CHEMISTRY-AN ASIAN JOURNAL
Volume 16, Issue 13, Pages 1685-1702

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202100277

Keywords

Alkyl enol ethers; ambiphilic nature; Intermolecular reactions

Funding

  1. Department of Science and Technology, Science and Engineering Research Board (SERB), India
  2. DST-INSPIRE
  3. MHRD, India

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Alkyl enol ethers (AEE) are versatile synthetic intermediates with unique reactivity patterns, capable of forming various bonds in intermolecular reactions. Their synthetic applications include metal-catalyzed reactions, cycloaddition, heterocycle formation, and reactions in natural product synthesis, showcasing their impressive potential in organic synthesis. The review aims to highlight the extensive use of AEE in reactions with both electrophiles and nucleophiles, demonstrating its ambiphilic reactivity and attracting chemists to explore AEE chemistry further. The intermolecular reactions of AEE with other functionalized moieties remain an unexplored area for future research.
Alkyl enol ethers (AEE) are versatile synthetic intermediates with a unique reactivity pattern. This review article summarizes the synthesis of AEE as well as its reactivity and how enol ether undergoes intermolecular reactions for various bond formation, leading to the construction of several useful organic molecules. The synthetic applications of alkyl enol ethers towards intermolecular bond-forming reactions include metal-catalyzed reactions, cycloaddition and heterocycle formation as well as rwactions in the field of natural products synthesis. The achievement of these impressive transformations prove the countless synthetic potential of AEE. The main objective of this review is to bring attentiveness among synthetic chemists to show how AEE extensively can be used to react with both electrophiles as well as nucleophiles, thereby behaving as an ambiphilic reactant. We trust that the unique reactivity pattern of alkyl enol ethers and the fundamental mechanistic idea can attract chemists in AEE chemistry. Exclusively, intermolecular reactions of AEE with other functionalized moieties have not been reviewed to the best of our knowledge.

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