Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives

Authors
Allin, SM Northfield, CJ Page, MI Slawin, AMZ
Citation
Sm. Allin et al., Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives, J CHEM S P1, 11, 2000, pp. 1715-1721
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Volume
11
Year of publication
2000
Pages
1715 - 1721
Database
ISI
SICI code
0300-922X(2000)11:<1715:ATTSON>2.0.ZU;2-T
Abstract
New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic gamma-lactam substrates as N-acyliminium ion precursors in reactions with carbon and hydride nucleophi les. Removal of the phenylglycinol derived chiral auxiliary can be achieved without loss of stereochemical integrity at the newly created asymmetric c entre, and we report a novel method for this key step using conc. sulfuric acid.