Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones: A Mechanistic Investigation.
Artikel i vetenskaplig tidskrift, 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

mechanisms

organic synthesis

Författare

Marcus Angelin

Andreas Fischer

Tore Brinck

Olof Ramström

Journal of Organic Chemistry

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

Vol. 75 17 5882-5887

Ämneskategorier

Teoretisk kemi

Organisk kemi

DOI

10.1021/jo100868z