Chemistry:Chiral phosphoric acid
From HandWiki
Short description: Esters of phosphoric acid with a chiral backbone
2-C
6H
4, 9-anthracenyl, and 2, 4, 6-iPr
3-C
6H
2 (commonly known as TRIP[1]).
In organic chemistry, chiral phosphoric acids are esters of phosphoric acid H
3PO
4 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
- ↑ Klussmann, Martin; Ratjen, Lars; Hoffmann, Sebastian; Wakchaure, Vijay; Goddard, Richard; List, Benjamin (September 2010). "Synthesis of TRIP and Analysis of Phosphate Salt Impurities" (in en). Synlett 2010 (14): 2189–2192. doi:10.1055/s-0030-1258505. ISSN 0936-5214. http://www.thieme-connect.de/DOI/DOI?10.1055/s-0030-1258505.
- ↑ "Chiral Phosphoric Acids". https://ascensusspecialties.my.salesforce.com/sfc/p/#2E000000pAb6/a/VN000001fwST/DC6l1xU1IdAond7c63caJGMUVVyHQMT8E9NYnREYLn4.
- ↑ 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.
- ↑ 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. PMID 28042185.
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