Novel synthesis of carbohydrate-derived organocatalysts and their application in asymmetric aldol reactions

Novel synthesis of carbohydrate-derived organocatalysts and their application in asymmetric aldol reactions
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碳水化合物衍生有机催化剂的新合成及其在不对称羟醛反应中的应用

DOI:
10.1016/j.catcom.2013.07.011
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发表时间:
2013-11
影响因子:
3.7
通讯作者:
Zhang, Pengfei
Zhang, Pengfei
中科院分区:
化学3区
文献类型:
--
作者:
Shen, Chao;Liao, Hanxiao;Shen, Fangyi;Zhang, Pengfei

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碳水化合物作为一类重要的手性骨架材料,以其廉价易得的优势而受到广泛的重视。以碳水化合物为原料,合成了一种新型脯氨酰胺有机催化剂,并将其应用于环己酮与多种芳香醛的直接不对称羟醛缩合反应。在温和的反应条件下,以较高的产率(高达99%)、良好的非对映选择性(高达> 98:2dr)和对映选择性(高达97% ee)获得了相应的羟醛产物。
Carbohydrate as a kind of important chiral scaffold is widely recognized for its obvious advantages cheap and readily available. A new type of prolinamide organocatalysts, derived from carbohydrate, was synthesized in high yield, and the novel organocatalysts were applied to the direct asymmetric aldol reactions of cyclohexanone and various aromatic aldehydes. The corresponding aldol products were obtained in high yields (up to 99%) with excellent diastereoselectivities (up to > 98:2 dr) and enantioselectivities (up to 97% ee) under mild reaction conditions.
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