chiral phosphoric acid

{{short description|Esters of phosphoric acid with a chiral backbone}}

File:Chiral phosphoric acid.png

In organic chemistry, chiral phosphoric acids are esters of phosphoric acid {{chem2|H3PO4}} 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.{{cite web |title=Chiral Phosphoric Acids |url=https://ascensusspecialties.my.salesforce.com/sfc/p/#2E000000pAb6/a/VN000001fwST/DC6l1xU1IdAond7c63caJGMUVVyHQMT8E9NYnREYLn4 |access-date=3 October 2024 |website=Strem Product Resources}} The conjugate bases are also used in generating chiral ion pairs.{{cite journal |doi=10.1021/cr5001496|title=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|year=2014|last1=Parmar|first1=Dixit|last2=Sugiono|first2=Erli|last3=Raja|first3=Sadiya|last4=Rueping|first4=Magnus|journal=Chemical Reviews|volume=114|issue=18|pages=9047–9153|pmid=25203602|doi-access=free}}

In one example, they are used to catalyze the asymmetric desymmetrization by monohydrolysis of a diester.{{cite journal |doi=10.15227/orgsyn.093.0075 |title=Enantioselective Synthesis of α,α-Disubstituted Lactones via a Chiral Brønsted Acid Catalyzed Intramolecular Cyclization |date=2016 |last1=Wilent |first1=Jennifer |last2=Qabaja |first2=G. |last3=Petersen |first3=K. S. |journal=Organic Syntheses |volume=93 |pages=75–87 |pmid=28042185 |pmc=5198840 }}