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A Bioinspired Catalytic Oxygenase Cascade to Generate Complex Oxindoles
Author(s) -
Wang Yao,
Bauer Jonathan O.,
Strohmann Carsten,
Kumar Kamal
Publication year - 2014
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.201403415
Subject(s) - allylic rearrangement , aldehyde , catalysis , aldol reaction , chemistry , yield (engineering) , cascade , combinatorial chemistry , oxygenase , surface modification , stereochemistry , organic chemistry , enzyme , materials science , metallurgy , chromatography
Catalytic, selective, and controlled oxidative functionalization of CH bonds using molecular oxygen as an oxidant remains highly desirable and equally challenging in the development of synthetic methodologies. Presented herein is a one‐pot oxygenase cascade reaction wherein a copper(I)‐catalyzed oxygenase reaction transforms the allylic methyl group in 3‐methylidene oxindoles into an aldehyde, which then undergoes an aldol–oxa‐Michael addition sequence with β‐ketoesters to yield dihydrofuran‐bearing oxindoles.