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

S D Dreher; K R Hornberger; S T Sarraf; J L Leighton

doi:10.1021/ol0063860

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

Org Lett. 2000 Oct 5;2(20):3197-9. doi: 10.1021/ol0063860.

Authors

S D Dreher¹, K R Hornberger, S T Sarraf, J L Leighton

Affiliation

¹ Department of Chemistry, Columbia University, New York, New York, 10027, USA.

PMID: 11009380
DOI: 10.1021/ol0063860

Abstract

1,3-Diol synthons, protected as acetonides or benzylidene acetals, may be synthesized efficiently from homoallylic alcohols and acetone or benzaldehyde 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 the reaction, which was determined to be reversible.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Acetals / chemical synthesis*
Alcohols / chemistry
Allyl Compounds / chemistry*
Benzaldehydes / chemistry
Catalysis
Magnetic Resonance Spectroscopy
Organomercury Compounds*

Substances

Acetals
Alcohols
Allyl Compounds
Benzaldehydes
Organomercury Compounds

Abstract

Publication types

MeSH terms

Substances

Grants and funding