STEREOSPECIFIC SYNTHESES OF XY-2-((PHENYLCHALCOGENO)METHYLENE)TETRAHYDROFURANS

Authors
YOSHIMATSU M NAITO M SHIMIZU H MURAOKA O TANABE G KATAOKA T
Citation
M. Yoshimatsu et al., STEREOSPECIFIC SYNTHESES OF XY-2-((PHENYLCHALCOGENO)METHYLENE)TETRAHYDROFURANS, Journal of organic chemistry, 61(23), 1996, pp. 8200-8206
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
23
Year of publication
1996
Pages
8200 - 8206
Database
ISI
SICI code
0022-3263(1996)61:23<8200:SSOX>2.0.ZU;2-A
Abstract
2-Ethoxy-4-(phenylchalcogeno)but-3-ynyl ketones 1-10 were reduced with LiBH4 in Et(2)O diastereoselectively to give 5-(phenylchalcogeno)pent -4-yn-1-ols 11-20. Treatment of the phenylchalcogen-substituted alkyny l alcohols 11-20 with t-BuOK in t-BuOH provided useful Z)-2-((phenylch alcogeno)methylene)tetrahydrofurans 21-31 stereoselectively.