Lewis acid mediated diastereoselective allylation of 3-menthyloxycarbonyl-5,6-dihydropyridin-4-ones

Authors
Brocherieux-Lanoy, S Dhimane, H Vanucci-Bacque, C Lhommet, G
Citation
S. Brocherieux-lanoy et al., Lewis acid mediated diastereoselective allylation of 3-menthyloxycarbonyl-5,6-dihydropyridin-4-ones, SYNLETT, (4), 1999, pp. 405-408
Citations number
10
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
4
Year of publication
1999
Pages
405 - 408
Database
ISI
SICI code
0936-5214(199904):4<405:LAMDAO>2.0.ZU;2-6
Abstract
Sakurai allylation of menthyl enoates 5a-c afforded adducts 7a-c with low t o excellent facial selectivity, depending on the Lewis acid employed to pro mote this 1,4-nucleophilic addition of allyltrimethylsilane. A chelated mod el was assumed to explain the observed diastereoselectivity.