A green synthetic method for the synthesis of -sulfonylimines was developed involving the straightforward condensation of sulfonamides with aldehydes under green and catalyst-free conditions, mediated by neutral AlO as an efficient and reusable dehydrating agent. -Sulfonylimines were produced in high yields and purity under simple experimental procedures.
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| http://dx.doi.org/10.1039/d2ra08304c | DOI Listing |
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Organocatalytic Enantioselective Synthesis of [5.7]-Fused ε-Sultam ,-Heterocycles via (3 + 2)-Annulation of Seven-Membered Cyclic -Sulfonylimines with γ-Hydroxy-α,β-Unsaturated Ketones.
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Henan Key Laboratory of Natural Medicine Innovation and Transformation, State Key Laboratory of Antiviral Drugs, Henan University, Kaifeng, Henan 475004, P. R. China.
A highly stereoselective protocol for the (3 + 2)-annulation of biphenyl-bridged seven-membered cyclic -sulfonylimines with γ-hydroxy-α,β-unsaturated ketones was developed. The reactions afforded a wide range of chiral [5.7]-fused ε-sultams bearing N-adjacent 1,3-stereocenters in excellent yields (93-98% yields) and high enantio/diastereoselectivities (up to >99% ee, >20:1 d.
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J Am Chem Soc
January 2024
The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, P. R. China.
Article Synopsis
- Asymmetric electrocatalysis presents a promising method for creating chiral molecules through innovative reaction pathways.
- The study introduces a novel approach to paired electrocatalysis, enabling simultaneous activation of reactants on both electrodes, which is more efficient than traditional methods.
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Enantioselective Synthesis of Biphenyl-Bridged ϵ-Sultams by Organocatalytic Mannich Reactions of Cyclic N-Sulfonylimines with Unactivated Ketones.
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Key Laboratory of Natural Medicine and, Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan, 475004, P. R. China.
A highly enantioselective Mannich reaction of biphenyl-bridged seven-membered cyclic N-sulfonylimines with methyl alkyl ketones is disclosed in this study. The reaction was performed under organocatalysis by using a quinine-derived primary amine as the catalyst in combination with a Brønsted acid as the co-catalyst. High yields (up to 89 %) and excellent enantioselectivities (up to 97 % ee) were observed.
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Department of Chemistry, Indiana University, 800 E. Kirkwood Ave., Bloomington, IN, 47401, USA.
The synthesis of polycyclic compounds is of high interest due to the prevalence of these motifs in drugs and natural products. Herein, we report on the stereoselective construction of 3D bicyclic scaffolds and azetidine derivatives by modulation of N-sulfonylimines to achieve either [4+2]- or [2+2]-cycloaddition reactions. The utility of the method was established by further modulation of the product.
View Article and Find Full Text PDFEco-friendly and efficient catalyst-free synthesis of -sulfonylimines from sulfonamides and aldehydes: crucial role of AlO as a reusable dehydrating agent.
RSC Adv
January 2023
Laboratoire de Développement Chimique, Galénique et Pharmacologique des Médicaments, Faculté de Pharmacie de Monastir, Université de Monastir Rue Avicenne 5000 Monastir Tunisia
A green synthetic method for the synthesis of -sulfonylimines was developed involving the straightforward condensation of sulfonamides with aldehydes under green and catalyst-free conditions, mediated by neutral AlO as an efficient and reusable dehydrating agent. -Sulfonylimines were produced in high yields and purity under simple experimental procedures.
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