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Synlett 2013; 24(8): 903-919
DOI: 10.1055/s-0032-1318497
DOI: 10.1055/s-0032-1318497
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A New Tool in the Toolbox: Electron-Withdrawing Group Activated Ruthenium Catalysts for Olefin Metathesis
Further Information
Publication History
Received: 22 January 2013
Accepted after revision: 04 March 2013
Publication Date:
05 April 2013 (online)
Abstract
This account describes the discovery and development of efficient electron-withdrawing group activated Hoveyda–Grubbs catalysts, including a nitro-substituted catalyst and their applications in the syntheses of complex molecules.
1 Introduction
2 EWG-Activated Hoveyda–Grubbs Complexes
2.1 The Discovery and the Story Behind It
2.2 The Nitro-Substituted Hoveyda–Grubbs Catalyst
2.3 pH-Responsive Catalysts
2.4 Fine-Tuning of the EWG Fragment
3 Applications of the Nitro-Substituted Hoveyda–Grubbs Catalyst in the Preparation of Compounds of Biological Relevance
3.1 Synthesis of BILN 2061
4 Concluding Remarks
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For recent comprehensive reviews on metathesis, see:
For reviews on synthetic applications of olefin metathesis, see:
For selected examples of applications of olefin metathesis, see:
For the Nobel Prize Lectures, see:
For chiral version of H2, see:
For mechanistic insights into olefin metathesis catalysts, see:
A faster initiator was obtained by Blechert’s group, see:
The formation of tetrasubstituted double bonds remains the domain of Schrock’s molybdenum catalysts; for a comprehensive review, see:
For recent examples of ruthenium-based catalysts for the metathesis of tetrasubstituted olefins, see:
For (–)-securinine, see:
For (+)-viroallo-securinine, see:
For an artificial photosynthesis model, see:
For other representative examples, see:
For recent applications of catalyst N2 in the synthesis of the hepatitis C antiviral agent BILN 2061, see:
For a “tetrameric” Hoveyda catalyst (G1 dendrimer), see:
For higher-generation dendrimeric Ru catalysts, see:
For examples of EWG-activated catalysts developed by other chemists, see:
For applications of Zhan’s catalyst 64, see:
For application of Mauduit’s catalyst 63, see: