Yb(OTf)(3)-catalyzed oxymercuration of homoallylic alcohol-derived hemiacetals and hemiketals

Authors
Dreher, SD Hornberger, KR Sarraf, ST Leighton, JL
Citation
Sd. Dreher et al., Yb(OTf)(3)-catalyzed oxymercuration of homoallylic alcohol-derived hemiacetals and hemiketals, ORG LETT, 2(20), 2000, pp. 3197-3199
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
20
Year of publication
2000
Pages
3197 - 3199
Database
ISI
SICI code
1523-7060(20001005)2:20<3197:YOOHAH>2.0.ZU;2-R
Abstract
1,3-Diol synthons, protected as acetonides or benzylidene acetals, may be s ynthesized efficiently from homoallylic alcohols and acetone or benzaldehyd e by oxymercuration of the derived hemiketals and hemiacetals with HgClOAc. The use of catalytic amounts of Yb(OTf)(3) is crucial to the success of th e reaction, which was determined to be reversible.