title: Acetic acid aldol reactions in the presence of trimethylsilyl trifluoromethanesulfonate.
abstract: In the presence of TMSOTf and a trialkylamine base, acetic acid undergoes aldol addition to non-enolizable aldehydes under exceptionally mild conditions. Acidic workup yields the beta-hydroxy carboxylic acid. The reaction appears to proceed via a three-step, one-pot process, including in situ trimethylsilyl ester formation, bis-silyl ketene acetal formation, and TMSOTf-catalyzed Mukaiyama aldol addition. Independently synthesized TMSOAc also undergoes aldol additions under similar conditions.
authors.affiliation: Gottwald Center for the Sciences, University of Richmond, Richmond, Virginia 23173, USA. wdowney@richmond.edu
authors.forename: C Wade
authors.initials: CW
authors.lastname: Downey
authors.forename: Miles W
authors.initials: MW
authors.lastname: Johnson
authors.forename: Daniel H
authors.initials: DH
authors.lastname: Lawrence
authors.forename: Alan S
authors.initials: AS
authors.lastname: Fleisher
authors.forename: Kathryn J
authors.initials: KJ
authors.lastname: Tracy