Asymmetric Synthesis of Enantiopure Pyrrolidines by C(sp<sup>3</sup>)−H Amination of Hydrocarbons
Yanis Lazib, Pascal Retailleau, Tanguy Saget, Benjamin Darses, Philippe Dauban
Abstract
The asymmetric synthesis of enantiopure pyrrolidines is reported via a streamlined strategy relying on two sequential C-H functionalizations of simple hydrocarbons. The first step is a regio- and stereoselective catalytic nitrene C-H insertion. Then, a subsequent diastereoselective cyclization involving a 1,5-hydrogen atom transfer (HAT) from a N-centered radical leads to the formation of pyrrolidines that can then be converted to their free NH-derivatives.
Topics & Concepts
Enantiopure drugNitreneAminationChemistryStereoselectivityCatalysisHydrogen atomCombinatorial chemistryStereochemistryEnantioselective synthesisOrganic chemistryGroup (periodic table)Catalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsRadical Photochemical Reactions