Lai Qi, Li Yang, Gong Zhiyong, Liu Qingwen, Wei Chiyu, Song Zhiguang
Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China.
Chirality. 2015 Dec;27(12):979-88. doi: 10.1002/chir.22540. Epub 2015 Oct 1.
Several novel chiral bifunctional L-thiazoline-thiourea derivatives were easily synthesized from commercially available L-cysteine in high yield. These catalysts were subsequently applied to the enantioselective Michael addition of acetylacetone to β-nitrostyrenes. The products with S configuration were obtained in 98% enantiomeric excess (ee) when the L-thiazoline-thiourea derivatives were used. A plausible transition state model is proposed to explain the observed enantioselectivities.
几种新型手性双功能L-噻唑啉-硫脲衍生物可以很容易地从市售的L-半胱氨酸高产率合成。随后将这些催化剂应用于乙酰丙酮与β-硝基苯乙烯的对映选择性迈克尔加成反应。当使用L-噻唑啉-硫脲衍生物时，得到了对映体过量（ee）为98%的S构型产物。提出了一个合理的过渡态模型来解释观察到的对映选择性。
