Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones: A Mechanistic Investigation
2010 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, no 17, 5882-5887 p.Article in journal (Refereed) Published
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 analogue synthesis and DFT calculations. Direct diastereoselective crystallization from the reaction mixture was also achieved and studied for a number of substrates. Furthermore, the 3-substituted isoindolinones are an interesting group of compounds, both present important natural products, as well as being precursors to other valuable building blocks.
Place, publisher, year, edition, pages
2010. Vol. 75, no 17, 5882-5887 p.
DYNAMIC COMBINATORIAL CHEMISTRY, DIELS-ALDER REACTIONS, ASYMMETRIC-SYNTHESIS, DRUG DISCOVERY, DERIVATIVES, RECEPTOR, ISOINDOLOBENZAZEPINE, 2-CYANOBENZALDEHYDE, ISOINDOLIN-1-ONES, AUXILIARIES
IdentifiersURN: urn:nbn:se:kth:diva-26826DOI: 10.1021/jo100868zISI: 000281180100011ScopusID: 2-s2.0-77956142428OAI: oai:DiVA.org:kth-26826DiVA: diva2:375180
FunderSwedish Research Council
QC 201012072010-12-072010-11-292011-02-11Bibliographically approved