Diastereoselective conjugate addition reactions of 2 '-hydroxypropiophenone to 2 '-hydroxychalcones - Synthesis and structural characterization of the diastereomers of (+/-)-3-aryl-1,5-bis(2-hydroxyphenyl)2,4-dimethyl-1,5-pentanediones

Citation
Ams. Silva et al., Diastereoselective conjugate addition reactions of 2 '-hydroxypropiophenone to 2 '-hydroxychalcones - Synthesis and structural characterization of the diastereomers of (+/-)-3-aryl-1,5-bis(2-hydroxyphenyl)2,4-dimethyl-1,5-pentanediones, EUR J ORG C, (7), 1999, pp. 1739-1744
Citations number
27
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434-193X → ACNP
Issue
7
Year of publication
1999
Pages
1739 - 1744
Database
ISI
SICI code
1434-193X(199907):7<1739:DCARO2>2.0.ZU;2-9
Abstract
The diastereoselective synthesis of 3-aryl-1,5-bis(2-hydroxyphenyl)-2,4-dim ethyl-1,5-pentanediones has been carried out by conjugate addition reaction s of 2'-hydroxypropiophenone to 2'-hydroxy-alpha-methylchalcone derivatives , or in single one-pot reactions of 2'-hydroxypropiophenone with appropriat e benzaldehyde derivatives. The structures and stereochemistry of the obtai ned diastereomers have been determined using various NMR techniques, and th e factors determining their formation are investigated and discussed.