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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 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 PDFEnantiocontrolled Cyclization to Form Chiral 7- and 8-Membered Rings Unified by the Same Catalyst Operating with Different Mechanisms.
J Am Chem Soc
January 2025
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
Chiral medium-sized rings, albeit displaying attractive properties for drug development, suffer from numerous synthetic challenges due to difficult cyclization steps that must take place to form these unusually strained, atropisomeric rings from sterically crowded precursors. In fact, catalytic enantioselective cyclization methods for the formation of chiral seven-membered rings are unknown, and the corresponding eight-membered variants are also sparse. In this work, we present a substrate preorganization-based, enantioselective, organocatalytic strategy to construct seven- and eight-membered rings featuring chirality that is intrinsic to the ring in the absence of singular stereogenic atoms or single bond axes of chirality.
View Article and Find Full Text PDFOrganocatalytic Activation of Alkynes Enabled Remote Control of Atroposelectivity via Vinylidene -Quinone Methides.
J Am Chem Soc
January 2025
Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China.
Axially chiral -VQMs have been extensively investigated as key intermediates to approach miscellaneous chiral structures. By sharp contrast, their structural isomers -VQMs have not been previously documented. The major reason, which results in the significant delay, may ascribe to the inherent challenges in the enantioselective activation of alkynes in a remote manner.
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