Chiral Phosphoric Acids: Versatile Organocatalysts with Expanding Applications

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

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

Allylation
The enantioselective allylation of aldehydes can be accomplished under very mild conditions at non-cryogenic temperature (-30 °C).2

Allylation

Friedel-Crafts Alkylation
Functionalized indoles3,4 and pyrroles5 can be accessed in enantioenriched form by asymmetric alkylation.

Friedel-Crafts Alkylation

Product Information

View the complete Chiral Phosphoric Acids product portfolio.