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Synfacts 2009(2): 0211-0211
DOI: 10.1055/s-0028-1087594
DOI: 10.1055/s-0028-1087594
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Catalytic Asymmetric ”Aldol" Reaction
Y. Hayashi*, S. Samanta, T. Itoh, H. Ishikawa
Tokyo University of Science, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. Januar 2009 (online)
![](https://www.thieme-connect.de/media/synfacts/200902/lookinside/thumbnails/10.1055-s-0028-1087594-1.jpg)
Significance
Hayashi and co-workers describe a direct asymmetric organocatalytic self-aldol reaction of acetaldehyde. The reaction consumes three equivalents of acetaldehyde to afford the acetal 2 with an enantiomeric ratio of 91:9. For er determination and isolation, the authors found it necessary to derivatize the diastereomeric mixture 2 to butane-1,3-dibenzoate 3, which was obtained in an overall yield of 56%. Two further synthetic transformations which do not compromise the acetal’s enantiomeric excess are reported. The reaction is thought to proceed via enamine catalysis.