Yb(OTf)(3)-Catalyzed oxymercuration of homoallylic alcohol-derived hemiacetals and hemiketals.
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.
Dreher
S D
SD
Department of Chemistry, Columbia University, New York, New York, 10027, USA.
Hornberger
K R
KR
Sarraf
S T
ST
Leighton
J L
JL
D000080:Acetals / Q000138:chemical synthesis*; D000438:Alcohols / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D009941:Organomercury Compounds
D000080:Acetals; D000438:Alcohols; D000498:Allyl Compounds; D001547:Benzaldehydes; D009941:Organomercury Compounds