Catalytic Enantioselective Aminopalladation–Heck Cascade. Issue 13 (17th February 2021)

• Record Type: Journal Article
• Authors: He, Yu‐Ping; Cao, Jian; Wu, Hua; Wang, Qian; Zhu, Jieping
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 13(2021)
• Page Start: 7093
• Page End: 7097
• Publication Date: 2021-02-17
• Subjects: asymmetric synthesis -- domino reactions -- homogeneous catalysis -- nucleopalladation -- oxidative Heck reactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202016001
• Languages: English
• ISSNs: 1433-7851

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 O2 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. Abstract : Reaction of 2‐alkynylanilines with prochiral cyclopentenes in the presence of a catalytic amount of Pd(OAc)2, a chiral bidentate pyrox ligand and O2 as terminal oxidant affords structurally diverse indole‐cyclopentene conjugates bearing two stereocenters in a highly diastereo‐ and enantio‐selective manner.