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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Vydáno v:	Angewandte Chemie International Edition Ročník 60; číslo 13; s. 7093 - 7097
Hlavní autoři:	He, Yu‐Ping, Cao, Jian, Wu, Hua, Wang, Qian, Zhu, Jieping
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	WEINHEIM Wiley 22.03.2021 Wiley Subscription Services, Inc
Vydání:	International ed. in English
Témata:	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
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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. 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.
AbstractList	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. 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. 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.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. 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) , a chiral bidentate pyrox ligand and O 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. 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. 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.
Author	He, Yu‐Ping Wang, Qian Wu, Hua Cao, Jian Zhu, Jieping
Author_xml	– sequence: 1 givenname: Yu‐Ping surname: He fullname: He, Yu‐Ping organization: Ecole Polytechnique Fédérale de Lausanne – sequence: 2 givenname: Jian surname: Cao fullname: Cao, Jian organization: Hangzhou Normal University – sequence: 3 givenname: Hua surname: Wu fullname: Wu, Hua organization: Ecole Polytechnique Fédérale de Lausanne – sequence: 4 givenname: Qian surname: Wang fullname: Wang, Qian organization: Ecole Polytechnique Fédérale de Lausanne – sequence: 5 givenname: Jieping orcidid: 0000-0002-8390-6689 surname: Zhu fullname: Zhu, Jieping email: jieping.zhu@epfl.ch organization: Ecole Polytechnique Fédérale de Lausanne
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/33369004$$D View this record in MEDLINE/PubMed
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Keywords	ROUTE COMPLEXES ALKYNES oxidative Heck reactions INDOLES FUNCTIONALIZATION asymmetric synthesis homogeneous catalysis domino reactions TANDEM REACTION ISOCYANIDE INSERTION nucleopalladation CYCLIZATION
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Snippet	Domino processes initiated by intramolecular nucleopalladation of alkynes have been developed into powerful synthetic tools for the synthesis of functionalized...
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SubjectTerms	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
Title	Catalytic Enantioselective Aminopalladation–Heck Cascade
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