New highly asymmetric Henry reaction catalyzed by Cu(II) and a C(1)-symmetric aminopyridine ligand, and its application to the synthesis of miconazole |
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Authors: | Blay Gonzalo Domingo Luis R Hernández-Olmos Victor Pedro José R |
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Institution: | Departament de Química Orgànica, Facultat de Química, Universitat de València, Burjassot (València), Spain. gonzalo.blay@uv.es |
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Abstract: | 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. |
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Keywords: | aldol reaction antifungal agents asymmetric catalysis copper nucleophilic addition |
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