☆ 4.6 Article

Highly diastereo- and enantioselective direct Barbas-List aldol reactions promoted by novel benzamidoethyl and benzamidopropyl prolinamides in water

ORGANIC & BIOMOLECULAR CHEMISTRY (2011)

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ORGANIC & BIOMOLECULAR CHEMISTRY

卷 9, 期 3, 页码 935-940

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ROYAL SOC CHEMISTRY

DOI: 10.1039/c0ob00688b

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Chemistry, Organic

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Spanish DGICYT [CTQ2008-03960/BQU]
Junta de Castilla y Leon [GR 168]
Ministerio de Educacion y Ciencia

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摘要

Four novel benzamido-functionalized prolinamides have been prepared and tested as organocatalysts for enantioselective aldol reaction of aldehydes and cyclic ketones in water. In particular, prolinamide derived from achiral ethylene diamine was the best catalyst leading to anti aldols in excellent diastereomeric (up to 98/2) and enantiomeric (up to 99/1) ratios, thereby showing that lateral amide functionalities might be a key issue for facilitating in water chemistry. These catalysts are cheaper and easier to prepare than those previously described.

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