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

X Ariza; A M Costa; M Faja; O Pineda; J Vilarrasa

doi:10.1021/ol0062289

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

Org Lett. 2000 Sep 7;2(18):2809-11. doi: 10.1021/ol0062289.

Authors

X Ariza¹, A M Costa, M Faja, O Pineda, J Vilarrasa

Affiliation

¹ Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, 08028 Barcelona, Catalonia, Spain, EU.

PMID: 10964371
DOI: 10.1021/ol0062289

Abstract

[reaction: see text] 1,2-Diols react at rt with alkyl propynoates, in the presence of 4-dimethylaminopyridine, to give cyclic acetals which are quite stable to acid-catalyzed hydrolysis or methanolysis. 1,3-Diols and 1, 4-diols do not form acetals with alkyl propynoates under the same conditions. Deprotection is accomplished with bases (via elimination and addition/elimination steps).