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Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids.
Angew Chem Int Ed Engl. 2019 03 11; 58(11):3402-3406.AC

Abstract

The highly enantioselective addition of terminal ynamides to a variety of isatins, catalyzed by a bisoxazolidine copper complex under mild, base-free reaction conditions, is described. The reaction is broad in scope, scalable, applicable to unprotected isatins, and provides efficient access to 3-hydroxyoxindoles carrying a tetrasubstituted chiral center with excellent yields and enantioselectivities. Synthetically versatile, multifunctional 3-hydroxyindolinones are obtained by hydration, partial hydrogenation, or hydroxyacyloxylation of the ynamide moiety at room temperature and exhaustive hydrogenation followed by reductive detosylation and spontaneous cyclization affords cinchonamidine alkaloids.

Authors+Show Affiliations

Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC, 20057, USA.Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC, 20057, USA.

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

30695127

Citation

Moskowitz, Max, and Christian Wolf. "Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids." Angewandte Chemie (International Ed. in English), vol. 58, no. 11, 2019, pp. 3402-3406.
Moskowitz M, Wolf C. Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids. Angew Chem Int Ed Engl. 2019;58(11):3402-3406.
Moskowitz, M., & Wolf, C. (2019). Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids. Angewandte Chemie (International Ed. in English), 58(11), 3402-3406. https://doi.org/10.1002/anie.201814074
Moskowitz M, Wolf C. Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids. Angew Chem Int Ed Engl. 2019 03 11;58(11):3402-3406. PubMed PMID: 30695127.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids. AU - Moskowitz,Max, AU - Wolf,Christian, Y1 - 2019/02/14/ PY - 2018/12/10/received PY - 2019/01/28/revised PY - 2019/1/30/pubmed PY - 2020/9/15/medline PY - 2019/1/30/entrez KW - bisoxazolidines KW - chimonamidine KW - copper KW - isatins KW - ynamides SP - 3402 EP - 3406 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 58 IS - 11 N2 - The highly enantioselective addition of terminal ynamides to a variety of isatins, catalyzed by a bisoxazolidine copper complex under mild, base-free reaction conditions, is described. The reaction is broad in scope, scalable, applicable to unprotected isatins, and provides efficient access to 3-hydroxyoxindoles carrying a tetrasubstituted chiral center with excellent yields and enantioselectivities. Synthetically versatile, multifunctional 3-hydroxyindolinones are obtained by hydration, partial hydrogenation, or hydroxyacyloxylation of the ynamide moiety at room temperature and exhaustive hydrogenation followed by reductive detosylation and spontaneous cyclization affords cinchonamidine alkaloids. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/30695127/Catalytic_Enantioselective_Ynamide_Additions_to_Isatins:_Concise_Access_to_Oxindole_Alkaloids_ L2 - https://doi.org/10.1002/anie.201814074 DB - PRIME DP - Unbound Medicine ER -