Synthesis of Novel Thiazoline Catalysts and Their Application in Michael Addition Reaction  

作　　者：WANG Hongyue WANG Ze LI Shaoheng QIU Yuntao LIU Bowen SONG Zhiguang LIU Zhihui 

机构地区：[1]First Hospital of Jilin University, Changchun 130021, P. R. China [2]College of Chemistry, Jilin University, Changchun 130021, P. R. China [3]Stomatology Hospital of Jilin University, Changchun 130021, P. R. China

出　　处：《Chemical Research in Chinese Universities》2016年第3期373-377,共5页高等学校化学研究（英文版）

摘　　要：Several novel chiral thiazoline catalysts containing thiazoline, thiourea and proline were efficiently synthesized from commercially available L-cysteine. These ligands were subsequently applied to the asymmetric Michael reaction between cyclohexanone and various β-nitrostyrene. The result shows that the optimal catalyst for this reaction is ligand 18d, the organocatalyst with thiazoline, thiourea and chiral proline motif, which efficiently promotes the enantioselective conjugate addition of cyclohexanone to various nitroalkenes to yield the corresponding addition products in high to excellent yields with enantiomeric excess（e.e.） up to 95% and diastereoselectivity ratio（dr.） up to 99：1.Several novel chiral thiazoline catalysts containing thiazoline, thiourea and proline were efficiently synthesized from commercially available L-cysteine. These ligands were subsequently applied to the asymmetric Michael reaction between cyclohexanone and various β-nitrostyrene. The result shows that the optimal catalyst for this reaction is ligand 18d, the organocatalyst with thiazoline, thiourea and chiral proline motif, which efficiently promotes the enantioselective conjugate addition of cyclohexanone to various nitroalkenes to yield the corresponding addition products in high to excellent yields with enantiomeric excess（e.e.） up to 95% and diastereoselectivity ratio（dr.） up to 99：1.

关 键 词：Chiral thiazoline catalyst Michael reaction Asymmetric synthesis 

分 类 号：TQ423.2[化学工程] TB333[一般工业技术—材料科学与工程]