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Product‐Catalyzed Aldol Reaction between Trimethylsilyl Enolates and Aldehydes
Author(s) -
Fujisawa Hidehiko,
Nakagawa Takashi,
Mukaiyama Teruaki
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404084
Subject(s) - aldol reaction , ketene , chemistry , trimethylsilyl , lewis acids and bases , catalysis , alkoxide , aldol condensation , organic chemistry , lewis acid catalysis , medicinal chemistry
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.