Stereoselective syntheses of 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-diones

Authors
Katritzky, AR Xu, YJ He, HY Steel, PJ
Citation
Ar. Katritzky et al., Stereoselective syntheses of 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-diones, J CHEM S P1, (15), 2001, pp. 1767-1770
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
15
Year of publication
2001
Pages
1767 - 1770
Database
ISI
SICI code
1472-7781(2001):15<1767:SSO1>2.0.ZU;2-B
Abstract
1H-Imidazo[2,1-a]isoindole-2,5(3H,9bH)-diones 6a-i are synthesized in 67-96 % yields with high stereoselectivities (de 88-99%, except 6e with a 58% de value) via intermolecular condensation of 2-formylbenzoic acid (5) and alph a -amino amides 4a-i in the presence of a catalytic amount of toluene-p-sul fonic acid. Intermediates 4 are obtained in two steps from easily available chiral N-Boc-alpha -amino acids 1.