Premium
Cover Picture: Catalytic Enantioselective Synthesis of Oxindoles and Benzofuranones That Bear a Quaternary Stereocenter (Angew. Chem. Int. Ed. 33/2003)
Author(s) -
Hills Ivory D.,
Fu Gregory C.
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200390555
Subject(s) - stereocenter , enantioselective synthesis , oxindole , catalysis , chemistry , stereochemistry , organic chemistry
The enantioselective rearrangement of O ‐acylated benzofuranones and oxindoles with the generation of a quaternary stereocenter at C3 of the heterocycle is catalyzed by a planar‐chiral derivative of 4‐dimethylaminopyridine. As shown in the cover picture, the catalyst itself is red, whereas the resting state of the complex during the rearrangement of benzofurans is a green ion pair. Diazonamide A, an oxindole‐derived natural product with potent anticancer activity, is shown in the background. More on the asymmetric syntheses of such heterocycles is provided by I. D. Mills and G. C. Fu on page 3921 ff.