Enantio- and Diastereoselective Asymmetric Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes in a Doubly Stereocontrolled Manner Catalyzed by Bifunctional Rosin-Derived Amine Thiourea Catalysts
Enantio- and Diastereoselective Asymmetric Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes in a Doubly Stereocontrolled Manner Catalyzed by Bifunctional Rosin-Derived Amine Thiourea Catalysts
复制标题
双功能松香衍生胺硫脲催化剂催化 1,3-二羰基化合物与硝基烯烃的双立体控制对映和非对映选择性不对称加成
DOI：
10.1021/jo9009276
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发表时间：
2009-08-07
影响因子：
3.6
通讯作者：
Wang, Rui
中科院分区：
文献类型：
--
作者：
Jiang, Xianxing;Zhang, Yifu;Wang, Rui
以天然松香衍生物为原料，设计并合成了一类双功能松香胺硫脲催化剂。研究了1，3-二羰基化合物与硝基烯烃的双立体控制不对称加成反应。这些松香衍生的手性硫脲已被证明是作为有效的催化剂，这种双立体控制的有机催化过程中的硫脲催化剂的效率的调查与其他硫脲催化剂的报道相比。此外，这些手性硫脲。配体容易获得。此外，松香衍生的叔胺-硫脲也被发现是非常有效的构建连续的立体异构中心含有一个不对称的季碳通过迈克尔反应的α-取代的β-酮酯硝基烯烃。
Starting from commercially available natural rosin derivatives, a class of bifunctional rosin-derived amine thiourea catalysts were designed and synthesized. The doubly stereocontrolled asymmetric addition of a variety of 1,3-dicarbonyl compounds to nitroalkenes was investigated. These rosin-derived chiral thioureas have been shown to serve as effective catalysts for this double-sterecontrolled organocatalytic process by the investigation of the efficacy of the thiourea catalysts in comparison with other thiourea catalysts reported. In addition, these chiral thiourea. ligands are easily available. Furthermore, the rosin-derived tertiary amine-thiourea was also revealed to be highly efficient for construction of contiguous stereogenetic centers containing an asymmetric quaternary carbon by the Michael reaction of alpha-substituted beta-ketoesters to nitroalkenes.