Halogenated salt assisted Cu-catalyzed asymmetric 1,4-borylstannation of 1,3-enynes: enantioselective synthesis of allenylstannes
Jialin Ye, Yang Liao, Hao Huang, Yang Liu, Dongmei Fang, Min Wang, Lianrui Hu, Jian Liao
Abstract
)/Cu complex as a catalyst, and the desired products, chiral allenylstannes, were first synthesized by asymmetric catalysis with satisfactory yields and enantioselectivies. In this protocol, a catalytic amount of additive, a halogenated salt, plays a crucial role in the success. Control experiments and theoretical studies disclosed that the four-membered ring transmetallation transition states which were stabilized by a halide anion are the key to yields and stereochemical outcomes.
Topics & Concepts
Enantioselective synthesisCatalysisSalt (chemistry)ChemistryCombinatorial chemistryOrganic chemistryStereochemistryCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis of Indole Derivatives