Iron-catalyzed stereoselective C-H alkylation for simultaneous construction of C-N axial and C-central chirality.

Autor: Zhang ZJ; Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany., Jacob N; Laboratoire d'Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg/Université de Haute-Alsace, ECPM, 67087, Strasbourg, France., Bhatia S; Department of Chemistry, University of Rochester, Rochester, NY, 14627, USA., Boos P; Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany., Chen X; Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany.; Department of Chemistry, Zhejiang University, 310027, Hangzhou, China., DeMuth JC; Department of Chemistry, University of Rochester, Rochester, NY, 14627, USA., Messinis AM; Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany., Jei BB; Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany., Oliveira JCA; Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany., Radović A; Department of Chemistry, University of Rochester, Rochester, NY, 14627, USA., Neidig ML; Inorganic Chemistry Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, OX1 3QR, UK. michael.neidig@chem.ox.ac.uk., Wencel-Delord J; Laboratoire d'Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg/Université de Haute-Alsace, ECPM, 67087, Strasbourg, France. wenceldelord@unistra.fr.; Institut für Organische Chemie, Universität Würzburg, 97074 Würzburg, Germany. wenceldelord@unistra.fr., Ackermann L; Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, 37077, Göttingen, Germany. Lutz.Ackermann@chemie.uni-goettingen.de.; Wöhler Research Institute for Sustainable Chemistry (WISCh), Georg-August-Universität Göttingen, 37077, Göttingen, Germany. Lutz.Ackermann@chemie.uni-goettingen.de.
Jazyk: angličtina
Zdroj: Nature communications [Nat Commun] 2024 Apr 25; Vol. 15 (1), pp. 3503. Date of Electronic Publication: 2024 Apr 25.
DOI: 10.1038/s41467-024-47589-7
Abstrakt: The assembly of chiral molecules with multiple stereogenic elements is challenging, and, despite of indisputable advances, largely limited to toxic, cost-intensive and precious metal catalysts. In sharp contrast, we herein disclose a versatile C-H alkylation using a non-toxic, low-cost iron catalyst for the synthesis of substituted indoles with two chiral elements. The key for achieving excellent diastereo- and enantioselectivity was substitution on a chiral N-heterocyclic carbene ligand providing steric hindrance and extra represented by noncovalent interaction for the concomitant generation of C-N axial chirality and C-stereogenic center. Experimental and computational mechanistic studies have unraveled the origin of the catalytic efficacy and stereoselectivity.
(© 2024. The Author(s).)
Databáze: MEDLINE
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