Chiral phosphoric acid explained

In organic chemistry, chiral phosphoric acids are esters of phosphoric acid that have chiral backbones. Well known examples include cyclic diesters derived from the BINOL and TADDOL motifs. These compounds are used in asymmetric catalysis as chiral Brønsted acids and/or hydrogen-bond donors.^[1] The conjugate bases are also used in generating chiral ion pairs.^[2]

In one example, they are used to catalyze the asymmetric desymmetrization by monohydrolysis of a diester.^[3]

Notes and References

1. Web site: Chiral Phosphoric Acids .
2. 10.1021/cr5001496. Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates. 2014. Parmar. Dixit. Sugiono. Erli. Raja. Sadiya. Rueping. Magnus. Chemical Reviews. 114. 18. 9047–9153. 25203602. free.
3. 10.15227/orgsyn.093.0075 . Enantioselective Synthesis of α,α-Disubstituted Lactones via a Chiral Brønsted Acid Catalyzed Intramolecular Cyclization . 2016 . Wilent . Jennifer . Qabaja . G. . Petersen . K. S. . Organic Syntheses . 93 . 75–87 . 28042185 . 5198840 .