Enantioselective Rhodium-Catalyzed Allylation of Aliphatic Imines: Synthesis of Chiral C-Aliphatic Homoallylic Amines
Wei-Sian Li, Ting-Shen Kuo, Meng-Chi Hsieh, Ming‐Kang Tsai, Ping‐Yu Wu, Hsyueh‐Liang Wu
Abstract
Reported herein is a method for the efficient syntheses of optically active 1-alkyl homoallylic amines in yields up to 95%, 13.5:1 dr, and 98% ee under mild, aqueous reaction conditions, via the Rh-catalyzed asymmetric allylation of aliphatic aldimines. This method provides a streamlined synthetic platform for the preparation of indolizidine and piperidine alkaloids, thus demonstrating its usefulness.
Topics & Concepts
ChemistryEnantioselective synthesisAldimineCatalysisRhodiumPiperidineIndolizidineOrganic chemistryOptically activeCombinatorial chemistryAlkylAlkaloidCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis