Zirconium-catalyzed asymmetric Kabachnik–Fields reactions of aromatic and aliphatic aldehydes

Dai, Yijing; Zheng, Li; Chakraborty, Debarshi; Borhan, Babak; Wulff, William D.

doi:10.1039/d1sc03222d

Cited by 9 publications

(5 citation statements)

References 39 publications

(17 reference statements)

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“…Among three-component condensation reactions, the addition of nucleophiles to in situ generated CN bonds has become an extremely useful process for the synthesis of various nitrogen-containing molecules such as α-amino phosphonates. Although some asymmetric three-component hydrophosphonylation reactions of a carbonyl, an amine, and a hydrophosphoryl compound to synthesize α-amino phosphonates have been reported, known as the Kabachnik–Fields reaction, − it is still difficult to achieve good enantioselectivity without transition-metal catalyst. , In addition, only tricoordinated and tetracoordinated hydrophosphoryl compounds have been studied in the Kabachnik–Fields reaction. Few pentacoordinated compounds with P–H bond were used in the three-component hydrophosphorylation reaction of aldehyde and amine.…”

Section: Resultsmentioning

confidence: 99%

Investigation of the Asymmetric Addition Reactions Induced by Pentacoordinated Hydrospirophosphorane Substrate

et al. 2023

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Pentacoordinated bisaminoacyl hydrospirophosphoranes were first found to induce the asymmetric addition reactions as a novel chiral organic framework. Asymmetric addition reactions of bisaminoacyl hydrospirophosphoranes with aromatic aldehyde and in situ generated imine were investigated, and the corresponding α-hydroxyspirophosphonates and α-amino spirophosphonates were obtained. The addition reaction of hydrospirophosphoranes with ΔP configuration showed better stereoselectivity than that with ΛP configuration, not only for the addition reaction to aromatic aldehyde but also to in situ generated imine. Furthermore, the stereochemical mechanisms of asymmetric addition reactions induced by pentacoordinated hydrospirophosphorane were proposed by 31P NMR tracing experiment and X-ray diffraction analysis.

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Section: Resultsmentioning

confidence: 99%

Investigation of the Asymmetric Addition Reactions Induced by Pentacoordinated Hydrospirophosphorane Substrate

et al. 2023

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“…Among the various methods, two methods are very popular; the three-component condensation reaction of dialkyl phosphite with a mixture of alde- hyde and amine 6 and hydrophosphorylation of imines. 7 Both methods need a Lewis acid catalysts, such as InCl 3 , 8 ZnCl 2 or Zn(OTf) 2 , 9 Zr(Oi-Pr) 4 , 10 NbCl 5 , 11 TsOH, 12 TsCl, 13 Mg(ClO 4 ) 2 , 14 Nano Ceria, 15 -CD-sulfonic acid, 16 methanesulfonic acid, 17 etc., in the solvent. 18 A series of microwave (MW)-assisted or thermal heating of three-component reactions were elaborated by our group 19 and continued by the other research groups.…”

Section: Scheme 1 Examples Of Some Of Aminophosphonic Acids With Biol...mentioning

confidence: 99%

An Efficient One-Pot Synthesis of 1-Aminophosphonates

et al. 2022

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1-Aminophosphonates are valuable compounds with wide range applications in biological and industry. Various reaction conditions and catalysts have been reported for the synthesis of 1-aminophosphonates via three components (dialkylphos-phite+aldehyde+amine) or two component reaction (dialkylphos-phite+imine). We report here a solvent-free synthesis of 1-aminophosphonates under very mild reaction condition. Three component condensation reactions of dialkyl phosphite, carbonyl compound, and an amine gave 1-aminophosphonate in good to excellent yield under solvent- and catalyst-free condition at ambient temperature. Hydrophosphorylation of imines in the presence of dialkylphosphite under same condition gave also 1-aminophosphonates in good to excellent yield. These results showed that the reaction needs no to any catalyst or solvent for activation. It seems a tautomeric form of dialkylphosphite (as one of the components) catalysed the reaction. The reaction yield decreased using any solvent. In addition, a novel method will be reported for the synthesis of N-deprotected 1-aminophosphonates (analogues of 1-amino acids) from N-PMP 1-aminophosphonate in the presence of TCCA. To understand the activity of the dialkylphosphite under solvent free condition, the DFT calculations have provided insight into the basis of this activity.

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“…The Kabachnik-Fields reaction 7 is the most efficient method for the synthesis of α-aminophosphonates, using various titanium-based catalysts, 8,9 silver, 10 indium, 11 copper, 12 bismuth, 13,14 zirconium, 15,16 cobalt, 17 iron 18 and nickel. 19 In addition to transition metals, rare earths have also been used to synthesise these molecules; Jang et al developed a one-pot, three-component synthesis of α-aminophosphonates using Yb (OTf) 3 as a Lewis acid catalyst.…”

Section: Introductionmentioning

confidence: 99%

Box–Behnken design for the optimisation of Kabachnik–Fields reaction catalysed by natural kaolinite clay under eco-friendly conditions

Boukachabia,

Guezane-Lakoud,

Bendjeffal

et al. 2024

React. Chem. Eng.

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Zirconium-catalyzed asymmetric Kabachnik–Fields reactions of aromatic and aliphatic aldehydes

Abstract: An effective catalyst has been developed for the three-component coupling of aldehydes, anilines and phosphites in an asymmetric catalytic Kabachnik-Fields reaction to give a-aminophosphonates. A catalyst was sought that would give high...

Cited by 9 publications

References 39 publications

Investigation of the Asymmetric Addition Reactions Induced by Pentacoordinated Hydrospirophosphorane Substrate

Investigation of the Asymmetric Addition Reactions Induced by Pentacoordinated Hydrospirophosphorane Substrate

An Efficient One-Pot Synthesis of 1-Aminophosphonates

Box–Behnken design for the optimisation of Kabachnik–Fields reaction catalysed by natural kaolinite clay under eco-friendly conditions

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