Oxymercuration of homoallylic alcohol derived hemiacetals: diastereoselective synthesis of protected 1,3-diols

S T Sarraf; J L Leighton

doi:10.1021/ol991370z

Oxymercuration of homoallylic alcohol derived hemiacetals: diastereoselective synthesis of protected 1,3-diols

Org Lett. 2000 Feb 10;2(3):403-5. doi: 10.1021/ol991370z.

Authors

S T Sarraf¹, J L Leighton

Affiliation

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

PMID: 10814334
DOI: 10.1021/ol991370z

Abstract

[reaction: see text] Protected 1,3-diol synthons may be synthesized efficiently from homoallyic alcohols and simple aldehydes by oxymercuration of the derived hemiacetals. The reactions are diastereoselective and proceed without the use of solvent. Both Hg(OAc)2 and HgClOAc are effective in the reaction, and the latter produces isolable organomercurial chlorides directly.

Publication types

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

MeSH terms

Acetals / chemistry*
Alcohols / chemistry
Organomercury Compounds / chemical synthesis
Organomercury Compounds / chemistry*
Organomercury Compounds / isolation & purification
Stereoisomerism
Thermodynamics

Substances

Acetals
Alcohols
Organomercury Compounds

Abstract

Publication types

MeSH terms

Substances

Grants and funding