Premium
Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids
Author(s) -
Moskowitz Max,
Wolf Christian
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201814074
Subject(s) - oxindole , chemistry , enantioselective synthesis , catalysis , isatin , moiety , combinatorial chemistry , organic chemistry
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.