Solvent-free asymmetric direct aldol reactions organocatalysed by recoverable ( S a)-binam- l-prolinamide

The combination of ( S a)-binam- l-Pro (5 mol %) and benzoic acid (10 mol %) was used as catalysts in the direct aldol reaction between different aliphatic ketones and 4-nitrobenzaldehyde under solvent-free reaction conditions. Three different procedures are assayed: magnetic stirring (method A), ma...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 18; no. 19; pp. 2300 - 2304
Main Authors Guillena, Gabriela, del Carmen Hita, María, Nájera, Carmen, Viózquez, Santiago F.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 27.09.2007
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ACCELERATION
CATALYSIS
BINAM-PROLINAMIDES
ACIDS
BACKBONE
PROLINE
GREEN
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Summary:The combination of ( S a)-binam- l-Pro (5 mol %) and benzoic acid (10 mol %) was used as catalysts in the direct aldol reaction between different aliphatic ketones and 4-nitrobenzaldehyde under solvent-free reaction conditions. Three different procedures are assayed: magnetic stirring (method A), magnetic stirring after previous dissolution in THF and evaporation (method B), and ball mill technique (method C), methods A and B being the simplest. These reaction conditions allowed us to reduce the amount of required ketone to 2 equiv to give the aldol product in similar reaction times and regio-, diastero-, and enantioselectivities than in organic or aqueous solvents.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2007.09.020