In Situ Quench Reactions of Enantioenriched Secondary Alkyllithium Reagents in Batch and Continuous Flow Using an I/Li-Exchange

Kremsmair, Alexander; Wilke, Henrik R. R.; Harenberg, Johannes H. H.; Bissinger, Benjamin R. G.; Simon, Matthias M. M.; Alandini, Nurtalya und Knochel, Paul (2022): In Situ Quench Reactions of Enantioenriched Secondary Alkyllithium Reagents in Batch and Continuous Flow Using an I/Li-Exchange. In: Angewandte Chemie International Edition, Bd. 62, Nr. 1

Abstract

We report a practical in situ quench (ISQ) procedure involving the generation of chiral secondary alkyllithiums from secondary alkyl iodides (including functionalized iodides bearing an ester or a nitrile) in the presence of various electrophiles such as aldehydes, ketones, Weinreb amides, isocyanates, sulfides, or boronates. This ISQ-reaction allowed the preparation of a broad range of optically enriched ketones, alcohols, amides, sulfides and boronic acid esters in typically 90-98 % ee. Remarkably, these reactions were performed at -78 degrees C or -40 degrees C in batch. A continuous flow set-up permitted reaction temperatures between -20 degrees C and 0 degrees C and allowed a scale-up up to a 40-fold without further optimization.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1433-7851
• Sprache: Englisch
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 491502892