Abstract
Prolinamido-glycoside catalyzed asymmetric aldol reaction in aqueous media is reported. The reactions are rapid and highly stereoselective when water is used as solvent. The stereoselectivities were under influence of configurations of a prolyl residue of the catalyst and α-chiral aldehydes. Water soluble prolinamido-glycoside catalysts are easily separable from reaction mixture and can be recycled and re-used several times.
Highlights
Proline catalyzed stereoselective aldol reaction is convenient method for the preparation of synthetic intermediates of natural products [1]
Amino acyl sugar derivatives have demonstrated as water compatible organocatalysts, and prolinamido-glycosides, methyl 2-(L-prolyl)amido-α-D-glucopyranoside 1 and methyl 2-(D-prolyl)amido-α-D-glucopyranoside 2, offer useful potential as catalysts for aqueous aldol reaction [11]
A change of solvent from water to DMSO markedly decreased setereoselectivity of the reactions. This result shows prolinamido-glycoside act as watercompatible organocatalyst
Summary
Proline catalyzed stereoselective aldol reaction is convenient method for the preparation of synthetic intermediates of natural products [1]. Water is regarded as an ideal solvent in terms of its environmental influence and low cost, proline and the analogs have not been shown to act as an asymmetric catalyst in aqueous media [2] [3]. Since proline and the analogs have shown decreased selectivity in water and do not seem to act as an aldolase [4] [5], development of water-compatible organocatalysts has been of interest, especially for prebiotic synthesis of carbohydrates [6]-[10]. Amino acyl sugar derivatives have demonstrated as water compatible organocatalysts, and prolinamido-glycosides, methyl 2-(L-prolyl)amido-α-D-glucopyranoside 1 and methyl 2-(D-prolyl)amido-α-D-glucopyranoside 2, offer useful potential as catalysts for aqueous aldol reaction [11]. The prolinamido-glycosides exhibited catalyzing the formation of aldol products with
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