Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202300113
Keywords
amino acid derivatives; amino sulfonamide; asymmetric aldol reaction; organocatalysis; threonine
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Novel threonine-derived amino sulfonamide organocatalysts were developed and successfully applied to asymmetric aldol reactions. The reactions produced anti-aldol adducts with high diastereo- and enantioselectivity when catalyzed by threonine-derived tosylamide, and syn-aldol adducts were obtained when using threonine-derived triflamide catalyst in reactions between alpha-siloxyacetone and aromatic aldehydes. In both cases, a significant improvement in diastereoselectivity was observed compared to threonine-derived carboxylic acid catalyst.
Novel threonine-derived amino sulfonamide organocatalysts were developed and applied to the asymmetric aldol reactions. The reactions of cyclohexanones with aromatic aldehydes catalyzed by the threonine-derived tosylamide provided anti-aldol adducts in good yield with high diastereo- and enantioselectivity. On the other hand, syn-aldol adducts were obtained in the reactions between alpha-siloxyacetone and aromatic aldehydes using threonine-derived triflamide catalyst. In both cases, a significant improvement in diastereoselectivity was observed compared to threonine-derived carboxylic acid catalyst.
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