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Chiral phosphoric acids: a chiral lobby for enantioselective C–H activation

Chemical Communications, 2023
Chiral phosphoric acids can interact in different ways with the substrate to induce chirality into the system. This review summarizes the use of chiral phosphoric acids in the exciting field of enantioselective C–H activation.
null Sumit   +2 more
openaire   +2 more sources

Chiral Phosphoric-Acid-Catalyzed Cascade Prins Cyclization

Organic Letters, 2019
Asymmetric Prins cyclization of in situ generated quinone methides and o-aminobenzaldehyde has been developed with chiral phosphoric acid as an efficient catalyst. This unconventional method provides a facile access to diverse functionalized trans-fused pyrano-/furo-tetrahydroquinoline derivatives in excellent yield and with excellent diastereo- and ...
Huai-Ri Sun   +6 more
openaire   +2 more sources

Reactions of Chiral Phosphorous Acid Diamides

Phosphorus, Sulfur, and Silicon and the Related Elements, 1993
Abstract Chiral phosphorous acid diamides were prepared from chiral C2 diamines via the sequential addition of PCl3 and H2O. Alternatively, addition of PCI3 and hydrogen sulfide yieded the analogous thiophosphorous acid diamides. Deprotonation of the phosphorous acids under a variety of conditions gave the anions which reacted smoothly with alkyl ...
Vincent Blazis   +3 more
openaire   +1 more source

Chiral Phosphoric Acid Catalyzed Stereoselective Spiroketalizations

Synlett, 2013
The spiroketal functionality is an important structural motif present in numerous natural products. The synthesis of chiral spiroketals is typically achieved under equilibrating conditions and only few asymmetric approaches are known. We have demonstrated that chiral phosphoric acids (CPAs) could serve as effective catalysts for enantioselective ...
Pavel Nagorny   +2 more
openaire   +1 more source

Chiral Phosphoric Acid-Catalyzed Enantioselective and Diastereoselective Spiroketalizations

Journal of the American Chemical Society, 2012
Catalytic enantioselective and diastereoselective spiroketalizations with BINOL-derived chiral phosphoric acids are reported. The chiral catalyst can override the inherent preference for the formation of thermodynamic spiroketals, and highly selective formation of nonthermodynamic spiroketals could be achieved under the reaction conditions.
Zhankui, Sun   +3 more
openaire   +2 more sources

Chiral phosphoric acid catalysis: from numbers to insights

Chemical Society Reviews, 2018
Chiral phosphoric acids (CPAs) have emerged as powerful organocatalysts for asymmetric reactions, and applications of computational quantum chemistry have revealed important insights into the activity and selectivity of these catalysts.
Rajat Maji   +2 more
openaire   +2 more sources

Synthesis of chiral amino cyclic phosphoric acids

Wuhan University Journal of Natural Sciences, 2000
Chiral amino cyclic phosphoric acids, 5-amino-2-hydroxy-4-(4-nitrophenyl)-1,3,2-dioxaphosphorinane 2-oxide and 2-hydroxy-4-(4-methylsulfonylphenyl)-5-phthalimido-1,3,2-dioxaphos phorinane 2-oxide are synthesized in good over yields (64.2% and 72.8% respectively) from 2-amino-1-aryl-1,3-propanediols.
Zhang Zhan   +5 more
openaire   +1 more source

Chiral Brønsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles

Angewandte Chemie, 2020
AbstractA new chiral Brønsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2‐aryl‐substituted N ...
Kai Yang   +11 more
openaire   +2 more sources

Asymmetric binary acid catalysis: chiral phosphoric acid as dual ligand and acid

Chem. Commun., 2013
Recently, chiral Brønsted acids as dual ligand and acid catalysts in the context of metal catalysis have been developed. Such binary catalytic systems synergistically integrate chiral Brønsted acids and metal catalysts as a result of their weakly coordinating behaviors.
Jian, Lv, Sanzhong, Luo
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Chiral Phosphoric Acid‐Catalyzed Enantioselective Synthesis of Axially Chiral Compounds Involving Indole Derivatives

The Chemical Record, 2023
AbstractIndoles are one of the most ubiquitous subclass of N‐heterocycles and are increasingly incorporated to design new axially chiral scaffolds. The rich profile of reactivity and N−H functionality allow chemical derivatization for enhanced medicinal, material and catalytic properties.
Jun, Kee Cheng, Bin, Tan
openaire   +2 more sources

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