Small peptides catalyze highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone: Unprecedented regiocontrol in aqueous media

Small peptides catalyze highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone: Unprecedented regiocontrol in aqueous media
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DOI:
10.1021/ol049141m
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发表时间:
2004-06-24
期刊:
影响因子:
5.2
通讯作者:
Jiang, YZ
Jiang, YZ
中科院分区:
化学1区
文献类型:
--
作者:
Tang, Z;Yang, ZH;Jiang, YZ

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基于L-脯氨酸的小肽已被开发为羟基丙酮与醛的不对称直接羟醛缩合反应的有效催化剂。手性1,4-二醇7,这是不利的产品在类似的羟醛缩合反应催化的醛缩酶或L-脯氨酸,得到了高产率和高达96%ee的对映选择性与肽3和4在水介质中。
[GRAPHICS]L-Proline-based small peptides have been developed as efficient catalysts for the asymmetric direct aldol reactions of hydroxyacetone with aldehydes. Chiral 1,4-diols 7, which are disfavored products in similar aldol reactions catalyzed by either aldolases or L-proline, were obtained in high yields and enantioselectivities of up to 96% ee with peptides 3 and 4 in aqueous media.