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Enantioselective catalysis and complexity generation from allenoates.

Bryan J Cowen¹, Scott J Miller

¹Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107, USA.

Chemical Society Reviews

|October 23, 2009

Summary

Lewis base catalysis enables complex molecule synthesis using allenoates and nucleophiles like phosphines and amines. This review highlights asymmetric reactions with chiral catalysts for advanced organic synthesis.

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Area of Science:

Organic Chemistry
Catalysis

Background:

Lewis base catalysis is a powerful tool for organic synthesis.
Allenoates are versatile substrates for various chemical transformations.
Phosphine and amine nucleophiles are key components in Lewis base catalysis.

Purpose of the Study:

To review methodologies for Lewis base catalyzed reactions involving allenoates.
To emphasize recent advancements in asymmetric catalysis using chiral Lewis bases.
To highlight the generation of molecular complexity through these reactions.

Main Methods:

Utilizing phosphine and amine nucleophiles in reactions with allenoates.
Employing electron-deficient olefins, imines, and aldehydes as coupling partners.
Developing and applying chiral Lewis base catalysts for asymmetric synthesis.

Main Results:

Established a range of suitable coupling partners for allenoate reactions.
Demonstrated the utility of Lewis base catalysis for generating molecular complexity.
Advanced asymmetric reactions using chiral Lewis base catalysts.

Conclusions:

Lewis base catalysis with allenoates provides efficient routes to complex molecules.
Chiral Lewis base catalysts are crucial for enantioselective synthesis.
This field offers significant potential for developing new synthetic methodologies.