New protecting groups for 1,2-diols (boc- and moc-ethylidene). Cleavage ofacetals with bases

Authors
Ariza, X Costa, AM Faja, M Pineda, O Vilarrasa, J
Citation
X. Ariza et al., New protecting groups for 1,2-diols (boc- and moc-ethylidene). Cleavage ofacetals with bases, ORG LETT, 2(18), 2000, pp. 2809-2811
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
18
Year of publication
2000
Pages
2809 - 2811
Database
ISI
SICI code
1523-7060(20000907)2:18<2809:NPGF1(>2.0.ZU;2-S
Abstract
1,5-Diols react at rt with alkyl propynoates, in the presence of 4-dimethyl aminopyridine, to give cyclic acetals which are quite stable to acid cataly zed hydrolysis or methanolysis, 1,3-Diols and 1,4-diols do not form acetals with alkyl propynoates under the same conditions, Deprotection is accompli shed with bases (via elimination and addition/elimination steps).