Convenient synthesis of a reactive ester homoenolate

✍ Scribed by Erin DiMauro; Albert J. Fry

• Book ID: 104262431
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 263 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01653-6

✦ Synopsis

Reaction between methyl 3-phenyl-3-trimethylsilylpropionate (8) and catalytic quantities of tetrabutylammonium triphenyldifluorosilicate (TBAT) effects desilylation to the corresponding homoenolate, which can be trapped by a variety of electrophiles. Rearrangement of the homoenolate to the more stable enolate was not observed. The reaction amounted to overall umpolung of methyl cinnamate, the ot,13-unsaturated ester from which 8 was prepared.