Litcius/Paper detail

Catalytic Enantioselective Aminopalladation–Heck Cascade

Yu‐Ping He, Jian Cao, Hua Wu, Qian Wang, Jieping Zhu

2020Angewandte Chemie International Edition58 citationsDOIOpen Access PDF

Abstract

Abstract Domino processes initiated by intramolecular nucleopalladation of alkynes have been developed into powerful synthetic tools for the synthesis of functionalized heterocycles. However, a catalytic enantioselective version of this class of reactions remains scarce. We report herein that reaction of 2‐alkynylanilines with prochiral cyclopentenes in the presence of a catalytic amount of Pd(OAc) 2 , a chiral bidentate pyrox ligand and O 2 as terminal oxidant affords the structurally diverse indole‐cyclopentene conjugates bearing two stereocenters in a highly diastereo‐ and enantio‐selective manner. One of the products is converted to a heavily functionalized tetracyclic indolinone derivative.

Topics & Concepts

Enantioselective synthesisStereocenterCatalysisChemistryCyclopenteneDominoIntramolecular forceCombinatorial chemistryIndole testLigand (biochemistry)Cascade reactionDenticityStereochemistryOrganic chemistryReceptorMetalBiochemistryCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality Synthesis