PDF herunterladen
Synfacts 2006(3): 0274-0274  
DOI: 10.1055/s-2006-931987
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Highly Diastereo- and Enantioselective Direct Aldol Reactions in Water

Contributor(s): Benjamin List, Subhas Chandra Pan
Y. Hayashi*, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, M. Shoji
Tokyo University of Science, Japan
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
21. Februar 2006 (online)

    Lizenzen und Reprints

Significance

Siloxyproline catalysts have been identified as effective catalysts for the enantioselective direct aldol reaction in water without using an organic solvent. With 10 mol% of catalyst 1, excellent enantioselectivities (over 95%) and anti selectivities (dr = 4.7:1-25:1) are obtained with different aromatic and aliphatic aldehydes. These selectivities are higher than for the reaction performed in organic solvents. Catalyst loadings can be reduced to 1 mol% and the use of acyclic ketones instead of cyclohexanone is also reported.