One-pot enol silane formation-Mukaiyama aldol-type addition to dimethyl acetals mediated by TMSOTf.
Various ketones, esters, amides, and thioesters add in high yield to dimethyl acetals in the presence of silyl trifluoromethanesulfonates and an amine base. Acetals derived from aryl, unsaturated, and aliphatic aldehydes are all effective substrates. The reaction proceeds in a single reaction flask, with no purification of the intermediate enol silane necessary.
Downey
C Wade
CW
Gottwald Center for the Sciences, University of Richmond, Richmond, Virginia 23173, USA. wdowney@richmond.edu
Johnson
Miles W
MW
Tracy
Kathryn J
KJ
D000080:Acetals / Q000737:chemistry*; D000098:Acetophenones / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000080:Acetals; D000098:Acetophenones; D000447:Aldehydes; D001547:Benzaldehydes; D008698:Mesylates; D012821:Silanes; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate; C116609:3-hydroxybutanal; C038699:acetophenone; C032175:benzaldehyde; C059033:1,1-dimethoxyethane