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Lewis Base Catalyzed Aldol Reaction of Trimethylsilyl Enolates with Aldehydes
Author(s) -
Mukaiyama Teruaki,
Fujisawa Hidehiko,
Nakagawa Takashi
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200290025
Subject(s) - chemistry , lewis acids and bases , trimethylsilyl , aldol reaction , pyridine , hypervalent molecule , solvent , catalysis , lithium (medication) , aldol condensation , base (topology) , medicinal chemistry , organic chemistry , medicine , mathematical analysis , mathematics , reagent , endocrinology
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 ).