Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones: A Mechanistic Investigation.

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)