Catalytic Enantioselective Aminopalladation–Heck Cascade

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‐a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 60; no. 13; pp. 7093 - 7097
Main Authors: He, Yu‐Ping, Cao, Jian, Wu, Hua, Wang, Qian, Zhu, Jieping
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 22.03.2021
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
Alkynes
asymmetric synthesis
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Cyclopentene
domino reactions
Enantiomers
homogeneous catalysis
Indoles
nucleopalladation
Oxidants
oxidative Heck reactions
Oxidizing agents
Physical Sciences
Science & Technology
ROUTE
COMPLEXES
ALKYNES
oxidative Heck reactions
INDOLES
FUNCTIONALIZATION
asymmetric synthesis
homogeneous catalysis
domino reactions
TANDEM REACTION
ISOCYANIDE INSERTION
nucleopalladation
CYCLIZATION
ISSN:1433-7851, 1521-3773, 1521-3773
Online Access:Get full text
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Description
Summary: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. 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.
Bibliography:These authors contributed equally to this work.
Swiss National Science Foundation (SNF)
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202016001