Enantioselective Addition of Sodium Bisulfite to Nitroalkenes. A Convenient Approach to Chiral Sulfonic Acids

Sheikhi, Ehsan; Rezaei, Narjes; Castilla, Alvaro; Sanz‐Marco, Amparo; Vila, Carlos; Muñoz, M. Carmen; Pedro, José R.; Blay, Gonzalo

doi:10.1002/ejoc.202101064

Cited by 4 publications

(5 citation statements)

References 48 publications

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“…Recently, Sheikhi et al demonstrated the potential of sodium bisulfite (NaHSO 3 ) as a new sulfur-based nucleophile for enantioselective organocatalytic conjugate addition to β-nitrostyrene derivatives. [60] The reaction was efficiently conducted in the presence of a Takemoto-type bifunctional thiourea catalyst (Cat-27), yielding excellent catalytic results. Notably, the reaction smoothly proceeded even in the case of β,βdisubstituted nitroalkene.…”

Section: Sulfur-based Nucleophiles In Conjugate Addition Reactionsmentioning

confidence: 99%

“…[5] The β‐nitro compounds with quaternary stereocenters formed via conjugate addition to β,β‐disubstituted nitroalkenes can be easily transformed into several important species such as β 2,2 ‐amino acids and γ‐aminobutyric acids (GABAs) [6,7,8] . Therefore, the past few decades have witnessed the extensive development of catalytic asymmetric conjugate additions to β,β‐disubstituted nitroalkenes and the emergence of the corresponding elegant strategies [9–60] …”

Section: Introductionmentioning

confidence: 99%

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Advances in Catalytic Asymmetric Construction of Quaternary Stereogenic Centers by Conjugate Addition to β,β‐Disubstituted Nitroalkenes

et al. 2023

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Quaternary stereogenic centers are of great importance because of their prevalence in a series of bioactive natural products and pharmaceuticals. Although the catalytic asymmetric construction of these highly congested centers poses a formidable challenge, this field has been extensively explored in the past few decades, and several elegant strategies, such as the asymmetric conjugate addition to β,β‐disubstituted nitroalkenes, have been developed. The resultant β‐nitro quaternary stereocenters can be conveniently transformed into the corresponding β‐amino quaternary stereocenters commonly found in bioactive compounds. This review summarizes the recent advances in the construction of all‐carbon quaternary or hetero‐carbon quaternary stereocenters via metal‐catalyzed and organocatalyzed asymmetric conjugate addition to β,β‐disubstituted nitroalkenes, focusing on the scope, applications, and mechanisms of these reactions.

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Section: Sulfur-based Nucleophiles In Conjugate Addition Reactionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Advances in Catalytic Asymmetric Construction of Quaternary Stereogenic Centers by Conjugate Addition to β,β‐Disubstituted Nitroalkenes

et al. 2023

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“…2021 年, Blay 课题组 [94] 和 Brière 课题组 [95] 先后报道了亚硫酸氢钠对 β-硝基苯乙烯在不同硫脲催化下的立体选择性加成反应, 并以优异产率和对映选择性获得了相应的 β-硝基磺酸衍生物(Eq. 47).…”

Section: β-硝基烯烃和醛被各种催化剂催化得到相应加成unclassified

Research Progress on Reactions Involving β-Nitrostyrene

Li,

Sun,

Zhao

et al. 2023

Chinese Journal of Organic Chemistry

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β-Nitrostyrene has a variety of biological activities and is also an important intermediate in organic synthesis, which can participate in a variety of chemical reactions due to its active chemical properties, and has attracted extensive attention from researchers. The reactions involving nitrostyrene compounds in recent years are summarized, and the reaction are divided into denitrification reactions and carbon-carbon double bonds according to reaction sites, expecting to provide a reference for new reactions with β-nitrostyrene compounds as substrates. Keywords β-nitrostyrene; denitrogenation reaction; carbon carbon double bond reaction β-硝基苯乙烯是重要的有机化合物, 广泛存在于具有多种生物活性的化合物结构和药物分子中, 其本身也具有抑制人端粒酶 [1] 、杀菌 [2][3] 及抗肿瘤 [4][5] 等活性. 近年来, 其在有机合成方向的应用也越来越被重视.

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“…16,18,19,39,45 As far as we know, synthesis of sulfonate gemini surfactants using natural linoleic acid as building blocks is rarely reported. Inspired by the reported work on organocatalyzed addition of NaHSO 3 to α,β-unsaturated alkenes by employing organic base catalysis [46][47][48][49][50] as well as our previous work on sulfonation of alkyl oleate with NaHSO 3 catalyzed by the TBPB/iron (III) chloride (FeCl 3 ) system, 32 we initiated our investigation on the synthesis of sulfonate gemini surfactants through the addition of NaHSO 3 to alkyl linoleate so as to find appropriate conditions using MLO as a model substrate Notably, SMLD was detected as the only product with varying the reaction time (Figure S7). Hence, 20 h was chosen as the optimal reaction time.…”

Section: Optimization Of Sulfonation Reaction Conditionsmentioning

confidence: 99%

Renewable dissymmetric sulfonate gemini surfactants from addition of sodium hydrogensulfite to alkyl linoleate

Jia

et al. 2022

AIChE Journal

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A new series of bio‐based sulfonate gemini surfactants was synthesized through esterification of renewable linoleic acid with various alcohols and subsequent sulfonation with readily available sodium hydrogensulfite (NaHSO3). Organocatalytic sulfonation of methyl linoleate with NaHSO3 by the triethylamine and tert‐butyl peroxybenzoate catalyst system was investigated, where a methyl linoleate conversion of 96.4% could be achieved while generating high purity product without tedious purification. Three resulting sodium alkyl linoleate disulfonates (SALDs) have been characterized by Fourier transform infrared, high‐performance liquid chromatography, LC–MS, high‐resolution mass spectrometry (HR–MS), nuclear magnetic resonance techniques, and thermogravimetric analysis. The physicochemical properties and surface properties of the SALDs at various concentrations were investigated. The results showed that the SALDs exhibited low Krafft temperature, high water solubility, foam stability (foam half‐life time could reach 15 min), emulsifying ability (emulsification time of 2.0 g/L is 192 s), and good thermal stability. This study enriches the family of anionic gemini surfactants and provides reference data for facile preparation of gemini surfactants.

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Enantioselective Addition of Sodium Bisulfite to Nitroalkenes. A Convenient Approach to Chiral Sulfonic Acids

Cited by 4 publications

References 48 publications

Advances in Catalytic Asymmetric Construction of Quaternary Stereogenic Centers by Conjugate Addition to β,β‐Disubstituted Nitroalkenes

Advances in Catalytic Asymmetric Construction of Quaternary Stereogenic Centers by Conjugate Addition to β,β‐Disubstituted Nitroalkenes

Research Progress on Reactions Involving β-Nitrostyrene

Renewable dissymmetric sulfonate gemini surfactants from addition of sodium hydrogensulfite to alkyl linoleate

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