Solvent-effects tuning the catalytic reactivity of prolinamides in asymmetric aldol reactions
Solvent-effects tuning the catalytic reactivity of prolinamides in asymmetric aldol reactions
复制标题
溶剂效应调节脯氨酰胺在不对称羟醛反应中的催化反应性
DOI：
10.1016/j.tetasy.2014.10.019
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发表时间：
2014-12-31
影响因子：
--
通讯作者：
Yang, Hua
中科院分区：
文献类型：
--
作者：
Huang, Xiang-Rong;Liu, Qi;Yang, Hua
合成了新型的脯氨酰胺类有机催化剂，并将其应用于不对称羟醛缩合反应。在有机溶剂中，脯氨酰胺与芳香醛形成稳定的咪唑烷酮类化合物。研究发现，在水相条件下，可以显著抑制不需要的咪唑烷酮中间体的生成，提高其催化活性。因此，在2-Me-THF或盐水中获得了高的化学产率(高达99%)和良好的非对映选择性(高达>；20：1dr)和对映体选择性(高达95%ee)。这一策略可以作为一种通用的解决方案，以提高作为有机催化剂的脯氨酰胺的性能。(C)2014爱思唯尔有限公司。保留所有权利。
Novel prolinamides were prepared and applied as organocatalysts in the asymmetric aldol reaction. Stable imidazolidinones were formed between prolinamides and aromatic aldehydes in organic solvents. It was found that aqueous conditions can significantly suppress the formation of the unwanted imidazolidinone intermediate and improve the catalytic activity of the prolinamides. As a consequence, high chemical yields (up to 99%) and good diastereoselectivity (up to >20:1 dr) and enantioselectivity (up to 95% ee) were achieved in 2-Me-THF or brine. This strategy could serve as a general solution to enhance the performance of prolinamides as organocatalysts. (C) 2014 Elsevier Ltd. All rights reserved.