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New Highly Asymmetric Henry Reaction Catalyzed by CuII and a C1-Symmetric Aminopyridine Ligand, and Its Application to the Synthesis of Miconazole

Authors

  • Gonzalo Blay Dr.,

    1. Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 59, 46100 Burjassot (València), Spain, Fax: (+34) 963-544-328
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  • Luis R. Domingo Dr.,

    1. Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 59, 46100 Burjassot (València), Spain, Fax: (+34) 963-544-328
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  • Victor Hernández-Olmos,

    1. Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 59, 46100 Burjassot (València), Spain, Fax: (+34) 963-544-328
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  • José R. Pedro Prof. Dr.

    1. Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 59, 46100 Burjassot (València), Spain, Fax: (+34) 963-544-328
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Abstract

A new catalytic asymmetric Henry reaction has been developed that uses a C1-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)2H2O (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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