Chiral Phosphoric Acids: Versatile Organocatalysts with Expanding Applications
Introduction
Advantages
Representative Applications
Product Information
Introduction
We are proud to offer a suite of BINOL-derived chiral phosphoric acids in our collection of products for asymmetric catalysis. This well established class of chiral Brønsted acid catalysts has been applied to an ever-increasing number of useful transformations.
![BINOL-derived chiral phosphoric acids BINOL-derived chiral phosphoric acids](/deepweb/assets/sigmaaldrich/marketing/global/images/technical-documents/articles/chemistry-and-synthesis/reaction-design-and-optimization/binol-derived/binol-derived.jpg)
Advantages
- Alternative to metal catalysts and chiral auxiliaries
- Both enantiomers of catalyst are available
- Relatively low catalyst loading (often 1-5 mol %)
- High selectivity at non-cryogenic reaction temperatures (-30 to 23 °C)
Representative Applications
Reductive Amination
One of the earliest demonstrations of chiral phosphoric acid catalysis is the metal-free reduction of imines with an organic reductant (Hantzsch ester) to give enantioenriched amines.1
![Reductive Amination Reductive Amination](/deepweb/assets/sigmaaldrich/marketing/global/images/technical-documents/articles/chemistry-and-synthesis/reaction-design-and-optimization/reductive-amination-application/reductive-amination-application.jpg)
Allylation
The enantioselective allylation of aldehydes can be accomplished under very mild conditions at non-cryogenic temperature (-30 °C).2
![Allylation Allylation](/deepweb/assets/sigmaaldrich/marketing/global/images/technical-documents/articles/chemistry-and-synthesis/reaction-design-and-optimization/allylation-application/allylation-application.jpg)
Friedel-Crafts Alkylation
Functionalized indoles3,4 and pyrroles5 can be accessed in enantioenriched form by asymmetric alkylation.
![Friedel-Crafts Alkylation Friedel-Crafts Alkylation](/deepweb/assets/sigmaaldrich/marketing/global/images/technical-documents/articles/chemistry-and-synthesis/reaction-design-and-optimization/friedel-crafts-application/friedel-crafts-application.jpg)
References
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