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Enantioselective Synthesis of Tetrahydro-1-1,3-methanocarbazoles by Formal (3 + 3)-Cycloaddition Using Bicyclo[1.1.0]butanes.
J Am Chem Soc
January 2025
Organisch-Chemisches Institut, Universität Münster, Corrensstraße 40, Münster 48149, Germany.
Asymmetric synthesis presents many challenges, with the selective formation of chiral bridged polyheterocycles being a notable example. Cycloadditions using bicyclo[1.1.
View Article and Find Full Text PDFAsymmetric Organocatalytic 1,6-Conjugate Addition of Alkynyl 8-Methylenenaphthalen-2(8)-one Formed In Situ: Synergistic Construction of Axial and Central Chirality.
Org Lett
January 2025
Taizhou Research Institute, Southern University of Science and Technology, Taizhou 318014, Zhejiang, China.
Organocatalytic enantioselective formal nucleophilic substitution reactions of α-(2-hydroxynaphthalen-8-yl)propargyl alcohols with 1-(1-indol-3-yl)naphthalen-2-ols have been established for the first time. With the aid of a suitable chiral phosphoric acid, alkynyl 8-methylenenaphthalen-2(8)-one was formed in situ from the corresponding α-(2-hydroxynaphthalen-8-yl)propargyl alcohol, followed by enantioselective 1,6-conjugate additions of 1-(1-indol-3-yl)naphthalen-2-ols to afford a number of enantioenriched (,)-2,3-disubstituted indoles in 50-80% yields with 81-93% ee and (,)-2,3-disubstituted indoles in 18-40% yields with 79-96% ee. Notably, these nucleophilic substitution products were characterized by the presence of functional groups, including indole, naphthol, and alkynyl units, while exhibiting both axial and central chirality.
View Article and Find Full Text PDFOrganocatalytic Packed-Bed Reactors for the Enantioselective Flow Synthesis of Quaternary Isotetronic Acids by Direct Aldol Reactions of Pyruvates.
Molecules
January 2025
Institute for Organic Synthesis and Photoreactivity of the Italian National Research Council, Area della Ricerca di Bologna, Via P. Gobetti, 101, 40129 Bologna, Italy.
The utilization of the homogeneous ()-2-pyrrolidine-tetrazole organocatalyst (Ley catalyst) in the self-condensation of ethyl pyruvate and cross-aldol reactions of ethyl pyruvate donor with non-enolizable pyruvate acceptors, namely the sterically hindered ethyl 3-methyl-2-oxobutyrate or the highly electrophilic methyl 3,3,3-trifluoropyruvate, is described as the key enantioselective step toward the synthesis of the corresponding biologically relevant isotetronic acids featuring a quaternary carbon functionalized with ester and alkyl groups. The transition from homogeneous to heterogeneous flow conditions is also investigated, detailing the fabrication and operation of packed-bed reactors filled with a silica-supported version of the pyrrolidine-tetrazole catalyst (SBA-15 as the matrix).
View Article and Find Full Text PDFPhysicochemical Characterization and Asymmetric Catalytic Properties of New Biobased Organocatalytic Surfactants.
Molecules
January 2025
Laboratoire de Chimie Agro-Industrielle (LCA), Université de Toulouse, INRAE, 4 allée Emile Monso, 31030 Toulouse, France.
In organic synthesis, the solvent is the chemical compound that represents the largest proportion of the process. However, conventional solvents are often toxic and dangerous for the environment, and an interesting alternative is to replace them by water. In this context, catalyst surfactants allow both organic reagents in water to be solubilized and organic reactions to be catalyzed.
View Article and Find Full Text PDFEnantioselective Decarboxylative Mannich Reactions of α,β-Unsaturated β'-Ketoacids and Isatin Imines: Application in the Synthesis of Spiro[indoline-3,2'-piperidine]-2,4'-diones.
Org Lett
January 2025
Department of Chemistry, Memorial University, St. John's, Newfoundland and Labrador A1B 3X7, Canada.
Organocatalytic, enantioselective decarboxylative Mannich reactions of α,β-unsaturated β'-ketoacids and isatin -Boc imines, to give the corresponding 3-carbamoyl-2-oxindole derivatives, were developed. Subsequent N-deprotection and diastereoselective, intramolecular, aza-Michael reaction of the free amine provides previously unreported spiro[indoline-3,2'-piperidine]-2,4'-diones.
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