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Synthesis of ketene N,N-acetals by copper-catalyzed double-amidation of 1,1-dibromo-1-alkenes.
Org Lett. 2009 Oct 01; 11(19):4454-7.OL

Abstract

An efficient procedure for the preparation of ketene N,N-acetals by copper-catalyzed double amidation of 1,1-dibromo-1-alkenes is reported. The reaction was found to be general, and ketene aminals could be obtained in good yields when potassium phosphate in toluene was used at 80 degrees C. The reaction was found to proceed through a regioselective monocoupling reaction followed by dehydrobromination and hydroamidation.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Coste A
Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, avenue des Etats-Unis, 78035 Versailles Cedex, France.
Couty F
No affiliation info available
Evano G
No affiliation info available

MeSH

AcetalsAlkenesAmidesCatalysisCopperMolecular StructureStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19775187

Citation

Coste, Alexis, et al. "Synthesis of Ketene N,N-acetals By Copper-catalyzed Double-amidation of 1,1-dibromo-1-alkenes." Organic Letters, vol. 11, no. 19, 2009, pp. 4454-7.
Coste A, Couty F, Evano G. Synthesis of ketene N,N-acetals by copper-catalyzed double-amidation of 1,1-dibromo-1-alkenes. Org Lett. 2009;11(19):4454-7.
Coste, A., Couty, F., & Evano, G. (2009). Synthesis of ketene N,N-acetals by copper-catalyzed double-amidation of 1,1-dibromo-1-alkenes. Organic Letters, 11(19), 4454-7. https://doi.org/10.1021/ol901831s
Coste A, Couty F, Evano G. Synthesis of Ketene N,N-acetals By Copper-catalyzed Double-amidation of 1,1-dibromo-1-alkenes. Org Lett. 2009 Oct 1;11(19):4454-7. PubMed PMID: 19775187.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of ketene N,N-acetals by copper-catalyzed double-amidation of 1,1-dibromo-1-alkenes. AU - Coste,Alexis, AU - Couty,François, AU - Evano,Gwilherm, PY - 2009/9/25/entrez PY - 2009/9/25/pubmed PY - 2009/12/16/medline SP - 4454 EP - 7 JF - Organic letters JO - Org Lett VL - 11 IS - 19 N2 - An efficient procedure for the preparation of ketene N,N-acetals by copper-catalyzed double amidation of 1,1-dibromo-1-alkenes is reported. The reaction was found to be general, and ketene aminals could be obtained in good yields when potassium phosphate in toluene was used at 80 degrees C. The reaction was found to proceed through a regioselective monocoupling reaction followed by dehydrobromination and hydroamidation. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19775187/Synthesis_of_ketene_NN_acetals_by_copper_catalyzed_double_amidation_of_11_dibromo_1_alkenes_ L2 - https://doi.org/10.1021/ol901831s DB - PRIME DP - Unbound Medicine ER -