Oxymercuration of homoallylic alcohol derived hemiacetals: diastereoselective synthesis of protected 1,3-diols.
[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.
Sarraf
S T
ST
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Leighton
J L
JL
D000080:Acetals / Q000737:chemistry*; D000438:Alcohols / Q000737:chemistry; D009941:Organomercury Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism; D013816:Thermodynamics
D000080:Acetals; D000438:Alcohols; D009941:Organomercury Compounds