Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones: A Mechanistic Investigation.
Journal article, 2010

The mechanism of a base-catalyzed one-pot reaction of 2-cyanobenzaldehyde and primary nitroalkanes, to produce 3-substituted isoindolinones, has been investigated. A route starting with a nitroaldol (Henry) reaction, followed by a subsequent cyclization and rearrangement, was supported by intermediate analog synthesis and DFT calcns. Direct diastereoselective crystn. from the reaction mixt. was also achieved and studied for a no. of substrates. Furthermore, the 3-substituted isoindolinones are an interesting group of compds., both present important natural products, as well as being precursors to other valuable building blocks. [on SciFinder(R)]

density functional theory


organic synthesis


Marcus Angelin

Andreas Fischer

Tore Brinck

Olof Ramström

Journal of Organic Chemistry

0022-3263 (ISSN) 1520-6904 (eISSN)

Vol. 75 17 5882-5887

Subject Categories

Theoretical Chemistry

Organic Chemistry



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