Article

Palladium-NHC catalyzed enantioselective synthesis of fused indolines via inert C(sp(3))-H activation.

Department of Organic Chemistry, University of Geneva, Geneva, Switzerland.
CHIMIA International Journal for Chemistry (impact factor: 1.21). 01/2012; 66(4):241-3. DOI:10.2533/chimia.2012.241 pp.241-3
Source: PubMed

ABSTRACT New sterically hindered chiral N-heterocyclic carbene (NHC) ligands were used in palladium catalysis to bring about a highly enantioselective C(sp(3))-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.

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Keywords

chiral N-heterocyclic carbene
 
cycloalkane moiety
 
enantioselective C(sp(3))-H activation
 
prochiral N-aryl-N-cycloalkyl methyl carbamate
 
temperatures
 

Masafumi Nakanishi