Temperature-Dependent Diastereodivergent [4 + 3] Annulation: Synthesis of Ferrocene-Fused Azepines via Rh(III) Catalysis
Raviraj Ananda Thorat, Devendra Parganiha, Saket Jain, Vipin Choudhary, Batul Shakir, Komal Rohilla, Raushan Kumar Jha, Sangit Kumar
Abstract
Herein, we disclose the first temperature-dependent diastereodivergent [4 + 3] annulation of ferrocene- p -tosylamides via C–H activation with allenes by a Rh catalyst. At room temperature, Rh-catalyzed [4 + 3] annulation selectively offered a kinetically controlled diastereomer [>20:1 diastereomeric ratio (dr)], whereas at 60 °C, a thermodynamically controlled diastereomer was obtained exclusively with >20:1 dr.
Topics & Concepts
ChemistryAnnulationFerroceneCatalysisCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryElectrochemistryPhysical chemistryElectrodeCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis