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Enantioselective Morita-Baylis-Hillman reaction of isatins with acrylates: facile creation of 3-hydroxy-2-oxindoles.
Org Lett. 2011 Jan 07; 13(1):82-5.OL

Abstract

The first tertiary amine catalyzed enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins with acrylates has been demonstrated, allowing asymmetric synthesis of biologically significant 3-substituted-3-hydroxy-2-oxindoles in good yields and with excellent enantioselectivities. The C6'-OH group of β-isocupreidine (β-ICD) is believed to facilitate the key proton transfer step in the MBH reaction, via an intramolecular proton relay process.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhong F
Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Republic of Singapore, 117543.
Chen GY
No affiliation info available
Lu Y
No affiliation info available

MeSH

AcrylatesCatalysisHydroxylationIndolesIsatinMolecular StructureOxindolesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21138329

Citation

Zhong, Fangrui, et al. "Enantioselective Morita-Baylis-Hillman Reaction of Isatins With Acrylates: Facile Creation of 3-hydroxy-2-oxindoles." Organic Letters, vol. 13, no. 1, 2011, pp. 82-5.
Zhong F, Chen GY, Lu Y. Enantioselective Morita-Baylis-Hillman reaction of isatins with acrylates: facile creation of 3-hydroxy-2-oxindoles. Org Lett. 2011;13(1):82-5.
Zhong, F., Chen, G. Y., & Lu, Y. (2011). Enantioselective Morita-Baylis-Hillman reaction of isatins with acrylates: facile creation of 3-hydroxy-2-oxindoles. Organic Letters, 13(1), 82-5. https://doi.org/10.1021/ol102597s
Zhong F, Chen GY, Lu Y. Enantioselective Morita-Baylis-Hillman Reaction of Isatins With Acrylates: Facile Creation of 3-hydroxy-2-oxindoles. Org Lett. 2011 Jan 7;13(1):82-5. PubMed PMID: 21138329.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Morita-Baylis-Hillman reaction of isatins with acrylates: facile creation of 3-hydroxy-2-oxindoles. AU - Zhong,Fangrui, AU - Chen,Guo-Ying, AU - Lu,Yixin, Y1 - 2010/12/03/ PY - 2010/12/9/entrez PY - 2010/12/9/pubmed PY - 2011/2/11/medline SP - 82 EP - 5 JF - Organic letters JO - Org Lett VL - 13 IS - 1 N2 - The first tertiary amine catalyzed enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins with acrylates has been demonstrated, allowing asymmetric synthesis of biologically significant 3-substituted-3-hydroxy-2-oxindoles in good yields and with excellent enantioselectivities. The C6'-OH group of β-isocupreidine (β-ICD) is believed to facilitate the key proton transfer step in the MBH reaction, via an intramolecular proton relay process. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21138329/Enantioselective_Morita_Baylis_Hillman_reaction_of_isatins_with_acrylates:_facile_creation_of_3_hydroxy_2_oxindoles_ L2 - https://doi.org/10.1021/ol102597s DB - PRIME DP - Unbound Medicine ER -