Acetic acid aldol reactions in the presence of trimethylsilyl trifluoromethanesulfonate.
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.
Downey
C Wade
CW
Gottwald Center for the Sciences, University of Richmond, Richmond, Virginia 23173, USA. wdowney@richmond.edu
Johnson
Miles W
MW
Lawrence
Daniel H
DH
Fleisher
Alan S
AS
Tracy
Kathryn J
KJ