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DOI: 10.1055/s-0031-1290131
Dual Activation in Organocatalysis: Design of Tunable and Bifunctional Organocatalysts and Their Applications in Enantioselective Reactions
Publication History
Publication Date:
19 January 2012 (online)
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Abstract
Dual activation has been identified as an important concept in the field of asymmetric catalysis, especially asymmetric organocatalysis. A comprehensive account of the design of novel amino hydrogen-bonding organocatalysts and their successful applications in two classic carbon-carbon bond forming reactions, namely the asymmetric aldol and Michael reactions, is given. This account also covers work that uses known organocatalysts in the preparation of other important chiral molecules using the asymmetric Michael reaction as the key transformation by virtue of a dual activation strategy.
1 Introduction
2 General Concept of Dual Activation
3 Dual Activation in Asymmetric Aldol Reactions
3.1 Design and Preparation of Tunable Aminoamide Organocatalysts
3.2 Application in the Asymmetric Aldol Reaction of Cyclic Ketones with Aldehydes
3.3 Application in the Asymmetric Aldol Reaction of Acetone with Isatins
3.4 Application in the Asymmetric Aldol Reaction of Acetone with Aldehydes
4 Dual Activation in Asymmetric Michael Reactions
4.1 Design and Preparation of Tunable Aminothiourea, Aminosalicylamide, and Aminosulfamide Organocatalysts
4.2 Application in the Asymmetric Michael Reaction of Cyclic Ketones and Nitroolefins
4.3 Application in the Asymmetric Michael Reaction of Bulky Aldehydes and Nitroolefins
4.4 Other Asymmetric Michael Reactions Based on a Dual Activation Strategy
5 Conclusion
Key words
asymmetric organocatalysis - dual activation - tunable organocatalysts - aldol reactions - Michael additions
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