Design of a binaphthyl-based axially chiral amino acid as an organocatalyst for direct asymmetric aldol reactions

作者：Kano Taichi; Tokuda Osamu; Takai Jun; Maruoka Keiji^*

来源：Chemistry-An Asian Journal, 2006, 1(1-2): 210-215.

DOI：10.1002/asia.200600077

• aldol reaction
• amino acids
• asymmetric catalysis
• biaryl compounds
• organocatalysis

A novel and robust binaphthyl-based amino acid was designed and successfully applied to the direct asymmetric aldol reaction. In some cases, this catalyst leads to higher yields and selectivities than the well-known proline catalyst. For instance, the direct asymmetric aldol reaction of acetone with 4-nitrobenzaldehyde in the presence of the binaphthyl-based amino acid catalyst proceeded smoothly to give the aldol adduct in 82% yield with 95% ee. This catalyst was also found to catalyze effectively the reactions of cyclic or unsymmetrical ketones to give the corresponding aldol adducts with excellent diastereo- and enantioselectivities.

• 出版日期2006-7