Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 50, Pages 16773-16778Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404241
Keywords
asymmetric alkylation; copper catalysis; enantioselectivity; N-heterocyclic carbenes; N-sulfonylimines
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Funding
- Japan Society for the Promotion of Science [24750037, 24350022]
- Grants-in-Aid for Scientific Research [24750037] Funding Source: KAKEN
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Amino acid-derived chiral imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene ligands. The copper-catalyzed asymmetric alkylation of various N-sulfonylimines with dialkylzinc reagents in the presence of these chiral imidazolium salts afforded the corresponding alkylated products with high enantioselectivity (up to 99% ee). The addition of HMPA to the reaction mixture as a co-solvent is critical in terms of chemical yield and enantioselectivity. A wide range of N-sulfonylimines and dialkylzinc reagents were found to be applicable to this reaction.
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