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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Popis
Shrnutí:	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.
Bibliografie:	These authors contributed equally to this work. Swiss National Science Foundation (SNF) ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ISSN:	1433-7851 1521-3773 1521-3773
DOI:	10.1002/anie.202016001