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 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.
Angelin
Marcus
M
KTH, Royal Institute of Technology, Department of Chemistry, Teknikringen 30, S-10044 Stockholm, Sweden.
Rahm
Martin
M
Fischer
Andreas
A
Brinck
Tore
T
Ramström
Olof
O
D000447:Aldehydes / Q000737:chemistry; D000473:Alkanes / Q000737:chemistry; D003198:Computer Simulation; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000473:Alkanes; D007211:Indoles