NOVEL SPIROACETAL SYNTHESIS VIA HYDROBORATION OF ALKYNEDIOLS

Authors
FUGAMI K HAGIWARA N OKEDA T KOSUGI M
Citation
K. Fugami et al., NOVEL SPIROACETAL SYNTHESIS VIA HYDROBORATION OF ALKYNEDIOLS, Chemistry Letters, (1), 1998, pp. 81-82
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
1
Year of publication
1998
Pages
81 - 82
Database
ISI
SICI code
0366-7022(1998):1<81:NSSVHO>2.0.ZU;2-#
Abstract
Alkynediols were transformed to the corresponding spiroacetals by the sequence of hydroboration with disiamylborane, oxidation of the result ing alkenylboron intermediate with alkaline hydrogen peroxide, and cat alytic treatment with p-TsOH. By this transformation, 6-(2-hydroxymeth yl)phenyl-3-methyl-5-hexyn-1-ol was converted to -3,2'-[4']methyl[3',4 ',5',6']tetrahydro-2'H-pyran] as a single diastereomer.