title: Chelation-controlled additions to α-silyloxy aldehydes: an autocatalytic approach.
abstract: The Felkin-Anh model has been widely accepted to describe stereochemical outcomes in nucleophilic additions to α-silyloxy carbonyl compounds. Herein, it is demonstrated that chelation-controlled additions can be performed using dialkylzinc reagents in the presence of chlorotrimethylsilane with good to excellent diastereoselectivities. Ethyl zinc chloride, the Lewis acid responsible for promoting chelation, is generated in situ in an autocatalytic fashion. This approach circumvents its use in stoichiometric amounts.
authors.affiliation: P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania , Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Ludovic
authors.initials: L
authors.lastname: Raffier
authors.forename: Gretchen R
authors.initials: GR
authors.lastname: Stanton
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes