Enantioselective Synthesis of β-Nitro Phosphonates Catalyzed by a Secondary Amine Bisthiourea

Nazish, Mohd; Jakhar, Ajay; Gupta, Naveen; Kureshy, Rukhsana I.

doi:10.1055/s-0037-1609683

Cited by 7 publications

(2 citation statements)

References 29 publications

(31 reference statements)

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“…In 2018, Khan and coworkers reported the asymmetric additio n of nitroalkenes with phosphites promoted by chiral secondary amine bisthio urea catalyst. 37 A variety of chiral βnitro phos phonates products were synthesized in good to high yields and enantioselectivities (Sc heme 32, 80%-90% yield, 75%-99% ee). A s eries of NMR studies indic ated that the hydrogen bonding interactio n between the catalyst a nd substrate should be exist ed, and a rational c atalytic mec hanism was establis hed for t his enantios electiv e Michael addition reaction.…”

Section: Scheme 31 Zn-catalyzed Asymmetric 14-addition Of Diethyl Pho...mentioning

confidence: 99%

Recent Advances in the Asymmetric Catalytic Synthesis of Phosphonates with an α-Chiral Center

et al. 2023

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Phosphonates and derivatives with α-chiral center are of great importance, and have been widely distributed in many natural products, pharmaceuticals and agrochemicals with various bioactive features. In the past decades, great effort has been made toward the development of efficient synthetic methods. In this Minireview, recent advances in asymmetric catalytic synthesis of phosphonates with α-chiral center are summarized, including asymmetric hydrogenation of α,β-unsaturated phosphonates, asymmetric addition of phosphonates to unsaturated electrophiles, and asymmetric addition of nucleophiles to α,β-unsaturated phosphonates. In addition, continuous development of enantioselective catalytic synthetic methods and the application of phosphonates and derivatives with α-chiral center is prospected in the future.

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Section: Scheme 31 Zn-catalyzed Asymmetric 14-addition Of Diethyl Pho...mentioning

confidence: 99%

Recent Advances in the Asymmetric Catalytic Synthesis of Phosphonates with an α-Chiral Center

et al. 2023

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“…However, despite the widespread use of these compounds, there are only a limited number of methods for their synthesis. [15][16][17][18][19][20][21][22][23][24][25][26] Construction of the P-C bond is one of the most significant steps in the synthesis of these compounds. For this purpose, the phospha-Michael, 27 Kabachnik-Fields, 28 Michaelis-Arbuzov, 29 and Pudovik 30 reactions are commonly used in forming P-C bonds for the preparation of organophosphorus compounds.…”

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confidence: 99%

Solvent-Free Synthesis of α-Cyanophosphonates from β-Nitrostyrenes using a Deep Eutectic Solvent

Shamsaddinimotlagh,

Ranjbari,

Tavakol

et al. 2024

Synlett

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New α-Cyanophosphonates, which are useful reagents for Horner-Wittig reaction, were synthesized in a solvent-free condition, using choline chloride-zinc chloride deep eutectic solvent (DES) as a catalyst. This work is only the second report on the synthesis of these compounds. In the previous report, diethyltrimethylsilylphosphite was used as a reagent and TiCl4 as a catalyst while in this study, both employed reagent and catalyst (triphenyl phosphine and choline chloride-zinc chloride DES) are cheaper, more available and less harmful than the previous work. Moreover, the reaction involves an interesting cascade reaction between β-nitrostyrenes and two equivalents of triphenylphosphite led to the desired product as a new synthetic route. These compounds can be used in the pharmaceutical and agricultural industries, in addition to their synthetic applications in the preparation of α,β-unsaturated nitriles. The reactions were completed using 20 mol% of DES at 80 °C in 6 hours. 10 different β-nitrostyrenes were synthesized in 55-87% yield after purification. β-nitrostyrenes containing electron-donating groups showed higher yields. The reaction was failed when aliphatic and heteroaromatic nitroalkenes and β-nitrostyrenes with electron-withdrawing substituent were employed. Finally, three plausible mechanistic routes were proposed for the reaction, starting from the nucleophilic addition of triphenylphosphite to α-carbon, nitrogen and oxygen atoms.

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Addition Reactions: Polar Addition

Kočovský

2021

Organic Reaction Mechanisms Series

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Enantioselective Synthesis of β-Nitro Phosphonates Catalyzed by a Secondary Amine Bisthiourea

Cited by 7 publications

References 29 publications

Recent Advances in the Asymmetric Catalytic Synthesis of Phosphonates with an α-Chiral Center

Recent Advances in the Asymmetric Catalytic Synthesis of Phosphonates with an α-Chiral Center

Solvent-Free Synthesis of α-Cyanophosphonates from β-Nitrostyrenes using a Deep Eutectic Solvent

Addition Reactions: Polar Addition

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