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Protecting group free, stereocontrolled synthesis of β-halo-enamides.
J Org Chem. 2012 Mar 02; 77(5):2149-58.JO

Abstract

Enamides, dienamides, and enynamides are important building blocks in synthetic, biological, and medicinal chemistry as well as materials science. Despite the extensive breath of their potential utility in synthetic chemistry, there is a lack of simple, high-yielding methods to deliver them efficiently and as single isomers. In this paper, we present a novel, protecting group free, efficient, and stereoselective approach to the generation of β-halo-enamides. The methodology presented provides a robust synthetic platform from which E- or Z-enamides can be generated in good yields and with complete stereocontrol.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Pasqua AE
School of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK.
Crawford JJ
No affiliation info available
Long DL
No affiliation info available
Marquez R
No affiliation info available

MeSH

AmidesCrystallography, X-RayModels, MolecularMolecular StructureStereoisomerism

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

22263777

Citation

Pasqua, Adele E., et al. "Protecting Group Free, Stereocontrolled Synthesis of Β-halo-enamides." The Journal of Organic Chemistry, vol. 77, no. 5, 2012, pp. 2149-58.
Pasqua AE, Crawford JJ, Long DL, et al. Protecting group free, stereocontrolled synthesis of β-halo-enamides. J Org Chem. 2012;77(5):2149-58.
Pasqua, A. E., Crawford, J. J., Long, D. L., & Marquez, R. (2012). Protecting group free, stereocontrolled synthesis of β-halo-enamides. The Journal of Organic Chemistry, 77(5), 2149-58. https://doi.org/10.1021/jo202130e
Pasqua AE, et al. Protecting Group Free, Stereocontrolled Synthesis of Β-halo-enamides. J Org Chem. 2012 Mar 2;77(5):2149-58. PubMed PMID: 22263777.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Protecting group free, stereocontrolled synthesis of β-halo-enamides. AU - Pasqua,Adele E, AU - Crawford,James J, AU - Long,De-Liang, AU - Marquez,Rodolfo, Y1 - 2012/02/14/ PY - 2012/1/24/entrez PY - 2012/1/24/pubmed PY - 2012/6/22/medline SP - 2149 EP - 58 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 5 N2 - Enamides, dienamides, and enynamides are important building blocks in synthetic, biological, and medicinal chemistry as well as materials science. Despite the extensive breath of their potential utility in synthetic chemistry, there is a lack of simple, high-yielding methods to deliver them efficiently and as single isomers. In this paper, we present a novel, protecting group free, efficient, and stereoselective approach to the generation of β-halo-enamides. The methodology presented provides a robust synthetic platform from which E- or Z-enamides can be generated in good yields and with complete stereocontrol. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/22263777/Protecting_group_free_stereocontrolled_synthesis_of_β_halo_enamides_ L2 - https://doi.org/10.1021/jo202130e DB - PRIME DP - Unbound Medicine ER -