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New highly asymmetric Henry reaction catalyzed by Cu(II) and a C(1)-symmetric aminopyridine ligand, and its application to the synthesis of miconazole.
Chemistry. 2008; 14(15):4725-30.C

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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Publisher Full Text (DOI)

Authors+Show Affiliations

Blay G
Departament de Química Orgànica, Facultat de Química, Universitat de València, Burjassot (València), Spain. gonzalo.blay@uv.es
Domingo LR
No affiliation info available
Hernández-Olmos V
No affiliation info available
Pedro JR
No affiliation info available

MeSH

4-AminopyridineCatalysisCopperLigandsMiconazoleMolecular StructureStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18384026

Citation

Blay, Gonzalo, et al. "New Highly Asymmetric Henry Reaction Catalyzed By Cu(II) and a C(1)-symmetric Aminopyridine Ligand, and Its Application to the Synthesis of Miconazole." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 14, no. 15, 2008, pp. 4725-30.
Blay G, Domingo LR, Hernández-Olmos V, et al. New highly asymmetric Henry reaction catalyzed by Cu(II) and a C(1)-symmetric aminopyridine ligand, and its application to the synthesis of miconazole. Chemistry. 2008;14(15):4725-30.
Blay, G., Domingo, L. R., Hernández-Olmos, V., & Pedro, J. R. (2008). New highly asymmetric Henry reaction catalyzed by Cu(II) and a C(1)-symmetric aminopyridine ligand, and its application to the synthesis of miconazole. Chemistry (Weinheim an Der Bergstrasse, Germany), 14(15), 4725-30. https://doi.org/10.1002/chem.200800069
Blay G, et al. New Highly Asymmetric Henry Reaction Catalyzed By Cu(II) and a C(1)-symmetric Aminopyridine Ligand, and Its Application to the Synthesis of Miconazole. Chemistry. 2008;14(15):4725-30. PubMed PMID: 18384026.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - New highly asymmetric Henry reaction catalyzed by Cu(II) and a C(1)-symmetric aminopyridine ligand, and its application to the synthesis of miconazole. AU - Blay,Gonzalo, AU - Domingo,Luis R, AU - Hernández-Olmos,Victor, AU - Pedro,José R, PY - 2008/4/4/pubmed PY - 2008/8/8/medline PY - 2008/4/4/entrez SP - 4725 EP - 30 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 14 IS - 15 N2 - 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. SN - 0947-6539 UR - https://www.unboundmedicine.com/medline/citation/18384026/New_highly_asymmetric_Henry_reaction_catalyzed_by_Cu_II__and_a_C_1__symmetric_aminopyridine_ligand_and_its_application_to_the_synthesis_of_miconazole_ DB - PRIME DP - Unbound Medicine ER -