Iron-Catalyzed Synthesis of Oxindoles: Application to the Preparation of Pyrroloindolines.

Org Lett

Departament of Fundamental Chemistry, Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, 05508-900, São Paulo, Brazil.

Published: March 2017

A novel and highly efficient synthetic approach to pyrroloindolines has been developed. The process is based on tandem radical addition/cyclization with inexpensive iron catalyst. This method tolerates a wide range of N-methyl-N-arylacrylamides as well carbamoyl radicals, providing access to a variety of functionalized 3,3-disubstituted oxindoles, key intermediates for many bioactive pyrroloindolines such as (±)-esermethole, (±)-deoxyeseroline, and (±)-physovenol methyl ether.

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http://dx.doi.org/10.1021/acs.orglett.7b00078DOI Listing

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