Diastereoselective one-pot tandem synthesis of 3-substituted isoindolinones: a mechanistic investigation.
Marcus Angelin, Martin Rahm, Andreas Fischer, Tore Brinck, Olof Ramström
文献索引:J. Org. Chem. 75(17) , 5882-7, (2010)
全文:HTML全文
摘要
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.
相关化合物
相关文献:
2015-01-01
[Beilstein J. Org. Chem. 11 , 2591-9, (2015)]
The aldol addition of readily enolizable 1, 3-dicarbonyl compounds to 2-cyanobenzaldehyde in the synthesis of novel 3-substituted isoindolinones. More V, et al.
[Synthesis 2011(18) , 3027-31, (2011)]
Application of baylis-hillman methodology in a new synthesis of 3-oxo-2, 3-dihydro-1H-isoindoles. Song YS, et al.
[J. Heterocycl. Chem. 40(5) , 939-42, (2003)]
Biotransformation of aromatic aldehydes and related compounds by Euglena gracilis Z. Noma Y, et al.
[Phytochemistry 30(9) , 2969-72, (1991)]
Novel synthesis of 3-(N-substituted amino)-1-isoindolenones from 2-cyanobenzaldehyde with amines. Sato R, et al.
[Chem. Lett. 9 , 1599-1602, (1984)]