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Enantioselective construction of 3-hydroxy oxindoles via decarboxylative addition of β-ketoacids to isatins.
Org Lett. 2012 Aug 03; 14(15):4018-21.OL

Abstract

The first highly enantioselective decarboxylative addition of β-ketoacids to isatins mediated by a bifunctional tertiary amine-thiourea catalyst has been developed, allowing facile synthesis of biologically important 3-hydroxy oxindoles in good yields and excellent enantioselectivities. The method reported represents a valuable approach of utilizing β-ketoacids as synthetic equivalents of aryl/alkyl methyl ketone enolates.

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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.
Yao W
No affiliation info available
Dou X
No affiliation info available
Lu Y
No affiliation info available

MeSH

CatalysisIndolesIsatinKeto AcidsMolecular StructureOxindolesStereoisomerismThiourea

Pub Type(s)

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

Language

eng

PubMed ID

22830448

Citation

Zhong, Fangrui, et al. "Enantioselective Construction of 3-hydroxy Oxindoles Via Decarboxylative Addition of Β-ketoacids to Isatins." Organic Letters, vol. 14, no. 15, 2012, pp. 4018-21.
Zhong F, Yao W, Dou X, et al. Enantioselective construction of 3-hydroxy oxindoles via decarboxylative addition of β-ketoacids to isatins. Org Lett. 2012;14(15):4018-21.
Zhong, F., Yao, W., Dou, X., & Lu, Y. (2012). Enantioselective construction of 3-hydroxy oxindoles via decarboxylative addition of β-ketoacids to isatins. Organic Letters, 14(15), 4018-21. https://doi.org/10.1021/ol301855w
Zhong F, et al. Enantioselective Construction of 3-hydroxy Oxindoles Via Decarboxylative Addition of Β-ketoacids to Isatins. Org Lett. 2012 Aug 3;14(15):4018-21. PubMed PMID: 22830448.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective construction of 3-hydroxy oxindoles via decarboxylative addition of β-ketoacids to isatins. AU - Zhong,Fangrui, AU - Yao,Weijun, AU - Dou,Xiaowei, AU - Lu,Yixin, Y1 - 2012/07/25/ PY - 2012/7/27/entrez PY - 2012/7/27/pubmed PY - 2012/12/12/medline SP - 4018 EP - 21 JF - Organic letters JO - Org Lett VL - 14 IS - 15 N2 - The first highly enantioselective decarboxylative addition of β-ketoacids to isatins mediated by a bifunctional tertiary amine-thiourea catalyst has been developed, allowing facile synthesis of biologically important 3-hydroxy oxindoles in good yields and excellent enantioselectivities. The method reported represents a valuable approach of utilizing β-ketoacids as synthetic equivalents of aryl/alkyl methyl ketone enolates. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/22830448/Enantioselective_construction_of_3_hydroxy_oxindoles_via_decarboxylative_addition_of_β_ketoacids_to_isatins_ L2 - https://doi.org/10.1021/ol301855w DB - PRIME DP - Unbound Medicine ER -