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Lewis Base Catalyzed Aldol Reaction of Trimethylsilyl Enolates with Aldehydes

โœ Scribed by Teruaki Mukaiyama; Hidehiko Fujisawa; Takashi Nakagawa

Publisher
John Wiley and Sons
Year
2002
Tongue
German
Weight
141 KB
Volume
85
Category
Article
ISSN
0018-019X

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โœฆ Synopsis

Abstract

A new Lewis base catalyzed aldol reaction of trimethylsilyl enolates with aldehydes is established in DMF or pyridine solvent by using a Lewis base such as lithium diphenylamide (Tablesโ€…4 and 5) or lithium 2โ€pyrrolidone (Tablesโ€…6โ€“8). The effect of solvent suggests that this reaction proceeds via the pentacoordinated hypervalent silicate generated by the coordination of the above Lewis base to a trimethylsilyl enolate. Successive coordination of the solvent to the thusโ€formed pentacoordinated silicate leads to an active enolate intermediate having hexacoordinated silicate, which, in turn, attacks carbonyl compounds to form the desired aldols (Schemeโ€…5).

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## 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 initiallyโ€formed aldolate anion effectively worked to catalyze the reaction. The โ€œproductโ€c