Enantioselective Rhodium(I)-Catalyzed [3+2] Annulations of Aromatic Ketimines Induced by Directed CH Activations

Triple selectivity: Highly substituted indenylamines can be obtained with high enantioselectivity by formal [3+2] additions of aryl ketimines with internal alkynes. These rhodium(I)‐catalyzed processes proceed by selective CH activation of one of the two arene substituents, regioselective carbometa...

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Published inAngewandte Chemie International Edition Vol. 50; no. 47; pp. 11098 - 11102
Main Authors Tran, Duc N., Cramer, Nicolai
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 18.11.2011
WILEY‐VCH Verlag
Wiley
Subjects
alkynes
annulation
asymmetric catalysis
Chemistry
Chemistry, Multidisciplinary
CH activation
Physical Sciences
rhodium
Science & Technology
ORGANIC-SYNTHESIS
alkynes
asymmetric catalysis
C?H activation
CLEAVAGE
CARBON-HYDROGEN
H BOND ACTIVATION
FUNCTIONALIZATION
annulation
INTERMOLECULAR HYDROACYLATION
REGIOSELECTIVE SYNTHESIS
rhodium
CATALYZED DIRECT ARYLATION
BENZOIC-ACIDS
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Summary:Triple selectivity: Highly substituted indenylamines can be obtained with high enantioselectivity by formal [3+2] additions of aryl ketimines with internal alkynes. These rhodium(I)‐catalyzed processes proceed by selective CH activation of one of the two arene substituents, regioselective carbometalation of the alkyne, and enantioselective addition across the imine.
Bibliography:ArticleID:ANIE201105766
EPFL
istex:9B8E4DCC64C79298938877660F7778307135F844
European Research Council - No. 257891
ark:/67375/WNG-PFCFB4RC-Z
We thank Dr. R. Scopelliti for X-ray crystallographic analysis of compound 7 m. This work was supported by the EPFL, ETH Zurich (ETH-16 08-3), and a starting grant from the European Research Council under the European Community's Seventh Framework Program (FP7 2007-2013)/ERC Grant agreement no. 257891. We thank Solvias AG for MeOBiphep ligands and Takasago International Corporation for Segphos ligands.
ETH Zurich - No. ETH-16 08-3
We thank Dr. R. Scopelliti for X‐ray crystallographic analysis of compound
This work was supported by the EPFL, ETH Zurich (ETH‐16 08‐3), and a starting grant from the European Research Council under the European Community’s Seventh Framework Program (FP7 2007–2013)/ERC Grant agreement no. 257891. We thank Solvias AG for MeOBiphep ligands and Takasago International Corporation for Segphos ligands.
7 m
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201105766