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

CHIMIA (Apr 2012)

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

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

Affiliations

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. [email protected]

DOI: https://doi.org/10.2533/chimia.2012.241
Journal volume & issue: Vol. 66, no. 4

Abstract

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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.

Published in CHIMIA

ISSN: 0009-4293 (Print); 2673-2424 (Online)
Publisher: Swiss Chemical Society
Country of publisher: Switzerland
LCC subjects: Science: Chemistry
Website: http://chimia.ch

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