New N-Heterocyclic Carbene Ligand and Its Application in Asymmetric Nickel-Catalyzed Aldehyde/Alkyne Reductive Couplings

• Published in: Journal of the American Chemical Society Vol. 129; no. 31; pp. 9568 - 9569
• Main Authors: Chaulagain, Mani Raj, Sormunen, Grant J, Montgomery, John
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 08.08.2007; Amer Chemical Soc
• Subjects: Aldehydes - chemistry; Alkynes - chemistry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Hydrocarbons - chemical synthesis; Hydrocarbons - chemistry; Ligands; Macrocyclic Compounds - chemistry; Methane - analogs & derivatives; Methane - chemical synthesis; Methane - chemistry; Molecular Structure; Nickel - chemistry; Oxidation-Reduction; Physical Sciences; Science & Technology; Stereoisomerism; KETONES; CHIRAL RUTHENIUM CATALYSTS; (+)-ALLOPUMILIOTOXIN 267A; HYDROGENATION; ALLYLIC ALCOHOLS; ALKENE TRANSFER; ALKYNES; CYCLIZATION; METATHESIS; ZINC
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja072992f

A new chiral N-heterocyclic carbene ligand has been prepared and examined in nickel-catalyzed, asymmetric reductive couplings of aldehydes and alkynes. In comparison with related structures that have been largely examined in asymmetric ring-closing metathesis reactions, the new ligand provides superior yields and enantioselectivities in the nickel-catalyzed reductive couplings. The scope of asymmetric couplings in intermolecular variants as well as a 14-membered macrocyclization is illustrated.