Journal
CHEMCATCHEM
Volume 5, Issue 8, Pages 2395-2404Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201300313
Keywords
aldehydes; alkynes; asymmetric catalysis; metal catalysis; organocatalysis
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Funding
- Centre National de la Recherche Scientifique
- Ministere de l'Enseignement Superieur et de la Recherche (MESR)
- Ville de Paris
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The metallo-organocatalyzed enantioselective synthesis of various five-membered carbo-and heterocyclic structures through the merger of aminocatalysis with the catalytic indium(III) or copper(I) activation of alpha-disubstituted formyl alkynes is described. The use of indium trichloride associated with the (R)-1,1'-bis-(2-naphthylamine) ligand led to encouraging results with up to 85:15 enantiomeric ratio. After a careful examination of several other strategies, the best synergic catalytic system, which combines a chiral copper(I) complex with cyclohexylamine, afforded the enantioselective preparations of cyclopentane, indane, and pyrrolidine scaffolds with moderate to excellent control of the all-carbon quaternary stereogenic centers created through such cyclization processes.
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