Chiral Thiophosphoramidate‐Catalyzed Asymmetric Michael Addition of Ketones to Nitro Olefins
Chiral Thiophosphoramidate‐Catalyzed Asymmetric Michael Addition of Ketones to Nitro Olefins
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DOI：
10.1002/ejoc.201000069
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发表时间：
2010-04
影响因子：
2.8
通讯作者：
A. Lu;Ronghua Wu;Y. Wang;Zhenghong Zhou;Guiping Wu;Jian‐xin Fang;Chuchi Tang
中科院分区：
文献类型：
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作者：
A. Lu;Ronghua Wu;Y. Wang;Zhenghong Zhou;Guiping Wu;Jian‐xin Fang;Chuchi Tang
合成了一种新型的吡咯烷基手性（硫代）氨基磷酸酯。其中化合物（S，aR）-3d被证明是一种有效的双功能有机催化剂，用于酮与硝基烯烃的不对称Michael加成反应。以良好至优异的化学产率获得相应的加合物，具有高水平的非对映体和对映体选择性（高达>99：1 dr和99%ee）。
A novel type of pyrrolidine-based chiral (thio)phosphoramidates was synthesized. Among them, compound (S,aR)-3d was proven to be an effective bifunctional organocatalyst for the asymmetric Michael addition of ketones to nitro olefins. The corresponding adducts were obtained in good to excellent chemical yields with high levels of diastereo- and enantioselectivities (up to >99:1 dr and 99 % ee).