Design of a binaphthyl-based axially chiral amino acid as an organocatalyst for direct asymmetric aldol reactions
Design of a binaphthyl-based axially chiral amino acid as an organocatalyst for direct asymmetric aldol reactions
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DOI：
10.1002/asia.200600077
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发表时间：
2006-07-01
影响因子：
4.1
通讯作者：
Maruoka, Keiji
中科院分区：
文献类型：
--
作者：
Kano, Taichi;Tokuda, Osamu;Maruoka, Keiji
设计了一种新颖且稳定的联萘基氨基酸，并成功应用于直接不对称羟醛反应。在某些情况下，这种催化剂比众所周知的脯氨酸催化剂具有更高的产率和选择性。例如，在联萘基氨基酸催化剂存在下，丙酮与4-硝基苯甲醛的直接不对称羟醛反应顺利进行，得到羟醛加合物，收率82%，ee 95%。还发现该催化剂可以有效催化环状或不对称酮的反应，生成具有优异的非对映选择性和对映选择性的相应羟醛加合物。
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.