AN ACYLIMINIUM ION APPROACH TOWARDS THE SYNTHESIS OF BETA-SUBSTITUTED3,4-DIHYDROISOQUINALONE PROPIONATES

Authors
FISHER MJ GUNN BP UM S JAKUBOWSKI JA
Citation
Mj. Fisher et al., AN ACYLIMINIUM ION APPROACH TOWARDS THE SYNTHESIS OF BETA-SUBSTITUTED3,4-DIHYDROISOQUINALONE PROPIONATES, Tetrahedron letters, 38(33), 1997, pp. 5747-5750
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
33
Year of publication
1997
Pages
5747 - 5750
Database
ISI
SICI code
0040-4039(1997)38:33<5747:AAIATT>2.0.ZU;2-U
Abstract
A variety of alpha-methoxy amides were prepared either by selective re duction of the exocyclic carbonyl of a 2-acyl-3,4-dihydroisaquinolone and subsequent trapping of the resultant alpha-hydroxy amide with acid ic methanol or by reacting the sodium salt of 3,4-dihydroisoquinolone with a functionalized alpha-chloro ether. These intermediates were rea cted with 1-tert-butoxy-1-tert-butyldimethylsiloxy ethene in the prese nce of BF3 . Et2O providing access to beta-substituted isoquinolone pr opionates in good yield. (C) 1997 Elsevier Science Ltd.