Premium
Aerobic Radical‐Cascade Alkylation/Cyclization of α,β‐Unsaturated Amides: an Efficient Approach to Quaternary Oxindoles
Author(s) -
Biswas Promita,
Paul Subhasis,
Guin Joyram
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201603809
Subject(s) - chemistry , alkylation , stereocenter , reagent , alkyl , radical , radical cyclization , decarbonylation , substrate (aquarium) , amide , organic chemistry , cascade , combinatorial chemistry , catalysis , enantioselective synthesis , oceanography , chromatography , geology
An efficient method for the aerobic radical‐cascade alkylation/cyclization of α,β‐unsaturated amides to afford functionalized oxindoles with a C3 quaternary stereocenter is described. The process is based on the generation of valuable alkyl radicals through sustainable aerobic C−H activation of aldehydes followed by decarbonylation using O 2 as the sole oxidant. This method features a broad substrate scope, inexpensive alkyl radical precursors, and convenient reagents. Finally, the method was successfully applied to the synthesis of alkyl analogues of tetrahydrofuranoindoline and (±)‐esermethole.