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- Title
Lewis Base Catalyzed Aldol Reaction of Trimethylsilyl Enolates with Aldehydes.
- Authors
Mukaiyama, Teruaki; Fujisawa, Hidehiko; Nakagawa, Takashi
- 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 ( Tables 4 and 5) or lithium 2-pyrrolidone ( Tables 6- 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 thus-formed pentacoordinated silicate leads to an active enolate intermediate having hexacoordinated silicate, which, in turn, attacks carbonyl compounds to form the desired aldols ( Scheme 5).
- Publication
Helvetica Chimica Acta, 2002, Vol 85, Issue 12, p4518
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.200290025