Diastereoselective chelation-controlled additions to β-silyloxy aldehydes.
A general diastereoselective method for the addition of dialkylzincs and (E)-di- and (E)-trisubstituted vinylzinc reagents to β-silyloxy aldehydes is presented. This method employs alkyl zinc triflate and nonaflate Lewis acids and affords chelation-controlled products (6:1 to > 20:1 dr).
P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
Gretchen R
GR
Stanton
Meara C
MC
Kauffman
Patrick J
PJ
Walsh
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002614:Chelating Agents / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000438:Alcohols; D000447:Aldehydes; D002614:Chelating Agents; D009942:Organometallic Compounds; D015032:Zinc