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]
^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.
^"Chiral Phosphoric Acids" (PDF).
^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.
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In organic chemistry, chiralphosphoricacids are esters of phosphoricacid H3PO4 that have chiral backbones. Well known examples include cyclic diesters...
In chemistry, a phosphoricacid, in the general sense, is a phosphorus oxoacid in which each phosphorus (P) atom is in the oxidation state +5, and is...
under the definition given here (e.g., protonation of an imine by a chiralphosphoricacid), the extent of proton transfer and the demarcation between hydrogen...
simple base. Phosphoricacid ( H 3 PO 4 {\displaystyle {\ce {H3PO4}}} ) is tribasic. For a more rigorous treatment of acid strength see acid dissociation...
contribute chirality centred at nitrogen atom. In this case, N-H bond acetylation product was also generated from the reaction. Chiralphosphoricacid-catalyzed...
with water to give phosphoricacid: P4O10 + 6 H2O → 4 H3PO4 Sulfur dioxide reacts with water to form the weak acid, sulfurous acid: SO2 + H2O → H2SO3...
dissociation of successive protons as Ka2, etc. Phosphoricacid, H3PO4, is an example of a polyprotic acid as it can lose three protons. When the difference...
finding Green's function Chiralphosphoricacid, esters of phosphoricacid Cyclopropane fatty acid, a subgroup of fatty acids CPA superfamily, of transport...
imines. One cascade reaction is catalyzed by a chiralphosphoricacid: The reaction proceeds via a chiral iminium ion. Traditional metal-based catalysts...
including polystyrene sulfonate, solid phosphoricacid, niobic acid, and heteropolyoxometallates. Solid acids are used in catalysis in many industrial...
randomly distributed along the polymer chain, and racemized chiral center of aspartic acid is produced. There were many catalysts reported for improving...
the deprotonation of acids, K is known as Ka, the acid dissociation constant. Strong acids, such as sulfuric or phosphoricacid, have large dissociation...
which a mixture or paste of crystalline aspartic acid and concentrated phosphoricacid or polyphosphoric acid in a thin layer is heated to 200 °C for 2 to...
trifluoroacetic acid modified with a chiral imidazolidinone: Indole reacts with an enamide catalyzed by a chiral BINOL derived phosphoricacid: In the presence...
chiral (non-mirror-symmetric) units. Living organisms use molecules that have the same chirality (handedness): with almost no exceptions, amino acids...
their assembly. Also, cheap chiral protecting groups may often shorten an enantioselective synthesis (e.g. shikimic acid for oseltamivir). As a rule,...
treatment with phosphoricacid. The final product is obtained in high purity (99.7%) and an overall yield of 17-22% from (−)-shikimic acid. It is noted...
equilibria. Other examples of inorganic polyprotic acids include anions of sulfuric acid, phosphoricacid and hydrogen sulfide that have lost one or more...
(EtO)2P(O)CHR-NHR' In addition to the Lewis-acid catalyzed Pudovik reaction, the reaction may be carried out in the presence of chiral amine bases. Catalytic amounts...
Mitsunobu; M. Yamada; T. Mukaiyama. (1967). "Preparation of Esters of PhosphoricAcid by the Reaction of Trivalent Phosphorus Compounds with Diethyl Azodicarboxylate...
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