Axially Chiral N,N-Ligand-Promoted Pd-Catalyzed Enantioselective Allylic Amination and Alkylation
Miaomiao Liu, Xiaotao Zhang, Rongrong Bao, Fangtao Xiao, Shouyi Cen, Zhipeng Zhang
Abstract
An axially chiral N,N-ligand developed from a [1,1'-binaphthalene]-2,2'-diol (BINOL)-based skeleton and phenanthroline is found to be capable of promoting Pd-catalyzed asymmetric allylic amination and alkylation of allyl acetates. The reaction is compatible with cyclic and acyclic secondary amines, primary aliphatic amines, malononitrile, and dialkyl malonates, affording the corresponding chiral products in up to 99% yield and with up to >99% enantiomeric excess.
Topics & Concepts
ChemistryAminationTsuji–Trost reactionEnantioselective synthesisLigand (biochemistry)CatalysisAlkylationEnantiomeric excessAllylic rearrangementYield (engineering)Medicinal chemistryChiral ligandOrganic chemistryCombinatorial chemistryMetallurgyMaterials scienceReceptorBiochemistryAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and Catalysis