Enantioselective Radical S<sub>N</sub>2-Type Alkylation of Morita–Baylis–Hillman Adducts Using Dual Photoredox/Palladium Catalysis
Xiangbin Bai, Linlin Qian, Hong‐Hao Zhang, Shouyun Yu
Abstract
An enantioselective radical alkylation of 4-alkyl-1,4-dihydropyridines with Morita–Baylis–Hillman (MBH) adducts has been reported. The SN2-type products are predominant. This reaction is enabled by dual photoredox/palladium catalysis. The alkylation products are provided in good yields with good regio- and enantioselectivity. The use of Ding’s spiroketal-based bis(phosphine) (SKP) ligand is crucial to achieving satisfactory regio- and enantioselectivity. The resultant α,β-unsaturated ester can be easily reduced to a synthetically useful chiral allyl alcohol.
Topics & Concepts
ChemistryEnantioselective synthesisAlkylationAdductPhosphineCatalysisPalladiumSN2 reactionAlkylTsuji–Trost reactionMedicinal chemistryCombinatorial chemistryOrganic chemistryStereochemistryRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods