Nickel‐Catalyzed Desymmetric Reductive Cyclization/Coupling of 1,6‐Dienes: An Enantioselective Approach to Chiral Tertiary Alcohol
Tianyuan Zhao, Li‐Jun Xiao, Qi‐Lin Zhou
Abstract
We have developed a nickel-catalyzed desymmetric reductive cyclization/coupling of 1,6-dienes. The reaction provides an efficient method for constructing a chiral tertiary alcohol and a quaternary stereocenter by a single operation. The method has excellent diastereoselectivity and high enantioselectivity, a broad substrate scope, as well as good tolerance of functional groups. Preliminary mechanism studies show that alkyl nickel(I) species are involved in the reaction.
Topics & Concepts
StereocenterEnantioselective synthesisNickelAlcoholCatalysisChemistryCombinatorial chemistryAlkylSubstrate (aquarium)Reductive eliminationFunctional groupOrganic chemistryCoupling (piping)StereochemistryMaterials scienceBiologyEcologyPolymerMetallurgyCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis