Product-Catalyzed Aldol Reaction between Trimethylsilyl Enolates and Aldehydes

✍ Scribed by Hidehiko Fujisawa; Takashi Nakagawa; Teruaki Mukaiyama

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 240 KB
• Volume: 346
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200404084

✦ Synopsis

Abstract

Aldol reactions between trimethylsilyl ketene acetals and aldehydes by using a catalytic amount of alkoxide anion proceeded smoothly to afford the corresponding aldols in DMF, indicating that the initially‐formed aldolate anion effectively worked to catalyze the reaction. The “product‐catalyzed aldol reaction”, a new class Lewis base‐catalyzed aldol reaction, between trimethylsilyl ketene acetals and aldehydes was performed successfully by the use of aldolate anion as a Lewis base catalyst.