6533b873fe1ef96bd12d56ad
RESEARCH PRODUCT
New highly asymmetric Henry reaction catalyzed by Cu(II) and a C(1)-symmetric aminopyridine ligand, and its application to the synthesis of miconazole.
Gonzalo BlayVictor Hernandez‐olmosLuis R. DomingoJosé R. Pedrosubject
Nitroaldol reactionNucleophilic additionNitromethaneMiconazoleMolecular StructureChemistryLigandOrganic ChemistryEnantioselective synthesisStereoisomerismStereoisomerismGeneral ChemistryLigandsMedicinal chemistryCatalysisCatalysischemistry.chemical_compoundAldol reactionOrganic chemistry4-AminopyridineCopperdescription
A new catalytic asymmetric Henry reaction has been developed that uses a C(1)-symmetric chiral aminopyridine ligand derived from camphor and picolylamine. A variety of aromatic, heteroaromatic, aliphatic, and unsaturated aldehydes react with nitromethane and other nitroalkanes in the presence of DIPEA (1.0 equiv), Cu(OAc)(2)*H(2)O (5 mol %), and an aminopyridine ligand (5 mol %) to give the expected products in high yields (up to 99 %), moderate-to-good diastereoselectivites (up to 82:18), and excellent enantioselectivities (up to 98 %). The reaction is air-tolerant and has been used in the synthesis of the antifungal agent miconazole.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2008-05-19 | Chemistry (Weinheim an der Bergstrasse, Germany) |