Palladium-NHC Catalyzed Enantioselective Synthesis of Fused Indolines via Inert C(sp3)-H Activation

Authors

  • Masafumi Nakanishi SCS-DSM Award for best poster presentation, Department of Organic Chemistry University of Geneva 30 Quai Ernest Ansermet CH-1211 Geneva 4, Switzerland
  • Dmitry Katayev Department of Organic Chemistry University of Geneva 30 Quai Ernest Ansermet CH-1211 Geneva 4, Switzerland
  • Céline Besnard Department of Condensed Matter Physics Section of Physics University of Geneva, Switzerland
  • E. Peter Kündig Department of Organic Chemistry University of Geneva 30 Quai Ernest Ansermet CH-1211 Geneva 4, Switzerland. peter.kundig@chiorg.unige.ch

DOI:

https://doi.org/10.2533/chimia.2012.241

Keywords:

Asymmetric catalysis, C–h activation, Chiral nhc, Indoline, Palladium

Abstract

New sterically hindered chiral N-heterocyclic carbene (NHC) ligands were used in palladium catalysis to bring about a highly enantioselective C(sp3)-H activation on the methylene site of a cycloalkane moiety. The intramolecular coupling reaction of a prochiral N-aryl-N-cycloalkyl methyl carbamate required high temperatures (140–160 °C) and afforded highly enantioenriched trans-2,3-fused indolines.
CHIMIA Vol. 66 No. 4 (2012): Laureates: Awards and Honors, SCS Fall Meeting

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Published

2012-04-25

Issue

Vol. 66 No. 4 (2012): Laureates: Awards and Honors, SCS Fall Meeting 2011

Section

Scientific Articles

License

Copyright (c) 2012 Swiss Chemical Society

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

How to Cite

[1]
M. Nakanishi, D. Katayev, C. Besnard, E. P. Kündig, Chimia 2012, 66, 241, DOI: 10.2533/chimia.2012.241.