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  • Title: A highly efficient organocatalyst for direct aldol reactions of ketones with aldehydes [corrected].
    Author: Tang Z, Yang ZH, Chen XH, Cun LF, Mi AQ, Jiang YZ, Gong LZ.
    Journal: J Am Chem Soc; 2005 Jun 29; 127(25):9285-9. PubMed ID: 15969611.
    Abstract:
    L-proline amides derived from various chiral beta-amino alcohols that bear substituents with various electron natures at their stereogenic centers are prepared and evaluated for catalyzing the direct Aldol reaction of 4-nitrobenzaldehyde with acetone. Catalysts with strong electron-withdrawing groups are found to exhibit higher catalytic activity and enantioselectivity than their analogues with electron-donating groups. The presence of 2 mol % catalyst 4g significantly catalyzes the direct Aldol reactions of a wide range of aldehydes with acetone and butanone, to give the beta-hydroxy ketones with very high enantioselectivities ranging from 96% to >99% ee. High diastereoselectivity of 95/5 was observed for the anti Aldol product from the reaction of cyclohexanone, and excellent enantioselectivity of 93% ee was provided for anti Aldol product from the reaction of cyclopentanone.
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