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Chiral phosphoric acid

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Structure of a common class of BINOL-derived chiral phosphoric acids. Catalysts of this type are also known as Akiyama–Terada catalysts (after Takahiko Akiyama and Masahiro Terada). Common examples of Ar include Ar = 4-NO2-C6H4, 9-anthracenyl, and 2, 4, 6-iPr3-C6H2 (commonly known as TRIP[1]).

In organic chemistry, chiral phosphoric acids are esters of phosphoric acid 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.[2] The conjugate bases are also used in generating chiral ion pairs.[3]

In one example, they are used to catalyze the asymmetric desymmetrization by monohydrolysis of a diester.[4]

References

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  1. ^ Klussmann, Martin; Ratjen, Lars; Hoffmann, Sebastian; Wakchaure, Vijay; Goddard, Richard; List, Benjamin (September 2010). "Synthesis of TRIP and Analysis of Phosphate Salt Impurities". Synlett. 2010 (14): 2189–2192. doi:10.1055/s-0030-1258505. ISSN 0936-5214.
  2. ^ "Chiral Phosphoric Acids". Strem Product Resources. Retrieved 3 October 2024.
  3. ^ Parmar, Dixit; Sugiono, Erli; Raja, Sadiya; Rueping, Magnus (2014). "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". Chemical Reviews. 114 (18): 9047–9153. doi:10.1021/cr5001496. PMID 25203602.
  4. ^ Wilent, Jennifer; Qabaja, G.; Petersen, K. S. (2016). "Enantioselective Synthesis of α,α-Disubstituted Lactones via a Chiral Brønsted Acid Catalyzed Intramolecular Cyclization". Organic Syntheses. 93: 75–87. doi:10.15227/orgsyn.093.0075. PMC 5198840. PMID 28042185.
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