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Aqueous Morita-Baylis-Hillman reaction of unprotected isatins with cyclic enones.
Org Lett. 2013 Nov 15; 15(22):5838-41.OL

Abstract

The readily available bicyclic imidazolyl alcohol 1 is a unique catalyst for the aqueous Morita-Baylis-Hillman (MBH) reaction between unprotected isatins and cyclic enones that gives access to a variety of potentially very useful 3-substituted 3-hydroxy-2-oxindoles in an operationally simple, efficient, and environmentally friendly way. The hydroxyl group of the catalyst is believed to stabilize the betaine intermediate formed in the first step of the MBH reaction.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Gomes JC
Departament de Química Orgànica, Universitat de Barcelona , Facultat de Química, Martí i Franquès 1-11, 08028-Barcelona, Catalonia, Spain, and Laboratory of Synthesis of Natural Products and Drugs, Institute of Chemistry, University of Campinas , P.O. Box 1654 - 13083-970, Campinas, SP - Brazil.
Sirvent J
No affiliation info available
Moyano A
No affiliation info available
Rodrigues MT
No affiliation info available
Coelho F
No affiliation info available

MeSH

BetaineCatalysisCycloparaffinsIsatinMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24188034

Citation

Gomes, Juliana C., et al. "Aqueous Morita-Baylis-Hillman Reaction of Unprotected Isatins With Cyclic Enones." Organic Letters, vol. 15, no. 22, 2013, pp. 5838-41.
Gomes JC, Sirvent J, Moyano A, et al. Aqueous Morita-Baylis-Hillman reaction of unprotected isatins with cyclic enones. Org Lett. 2013;15(22):5838-41.
Gomes, J. C., Sirvent, J., Moyano, A., Rodrigues, M. T., & Coelho, F. (2013). Aqueous Morita-Baylis-Hillman reaction of unprotected isatins with cyclic enones. Organic Letters, 15(22), 5838-41. https://doi.org/10.1021/ol4029034
Gomes JC, et al. Aqueous Morita-Baylis-Hillman Reaction of Unprotected Isatins With Cyclic Enones. Org Lett. 2013 Nov 15;15(22):5838-41. PubMed PMID: 24188034.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Aqueous Morita-Baylis-Hillman reaction of unprotected isatins with cyclic enones. AU - Gomes,Juliana C, AU - Sirvent,Jordi, AU - Moyano,Albert, AU - Rodrigues,Manoel T,Jr AU - Coelho,Fernando, Y1 - 2013/11/04/ PY - 2013/11/6/entrez PY - 2013/11/6/pubmed PY - 2014/4/20/medline SP - 5838 EP - 41 JF - Organic letters JO - Org Lett VL - 15 IS - 22 N2 - The readily available bicyclic imidazolyl alcohol 1 is a unique catalyst for the aqueous Morita-Baylis-Hillman (MBH) reaction between unprotected isatins and cyclic enones that gives access to a variety of potentially very useful 3-substituted 3-hydroxy-2-oxindoles in an operationally simple, efficient, and environmentally friendly way. The hydroxyl group of the catalyst is believed to stabilize the betaine intermediate formed in the first step of the MBH reaction. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/24188034/Aqueous_Morita_Baylis_Hillman_reaction_of_unprotected_isatins_with_cyclic_enones_ DB - PRIME DP - Unbound Medicine ER -