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

Masafumi Nakanishi; Dmitry Katayev; Céline Besnard; E. Peter Kündig

doi:10.2533/chimia.2012.241

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.