Highly enantio- and diastereoselective synthesis of α-trifluoromethyldihydropyrans using a novel bifunctional piperazine-thiourea catalyst

被引：62

作者：

Li, Peng ^{[1
,2
]}

Chai, Zhuo ^{[1
,2
]}

Zhao, Sheng-Li ^{[1
,2
]}

Yang, Ying-Quan ^{[1
,2
]}

Wang, Hai-Feng ^{[1
,2
]}

Zheng, Chang-Wu ^{[1
,2
]}

Cai, Yue-Peng ^{[3
]}

Zhao, Gang ^{[1
,2
]}

Zhu, Shi-Zheng ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Modern Synthet Organ Chem, Shanghai 200032, Peoples R China

[3] S China Normal Univ, Guangdong Univ, Sch Chem & Environm, Key Lab Technol Electrochem Energy Storage & Powe, Guangzhou 510006, Guangdong, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2009年 / 47期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE TRIFLUOROMETHYLATION; NUCLEOPHILIC-ADDITION; FLUOROMETHYL KETONES; MEDICINAL CHEMISTRY; MICHAEL ADDITION; MANNICH REACTION; ORGANOCATALYSTS; DERIVATIVES; NITROALKENES;

D O I：

10.1039/b915210e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective Michael addition of alpha-cyanoketones to alpha,beta-unsaturated trifluoromethyl ketones using a novel piperazine-thiourea catalyst was described. The resulting alpha-trifluoromethyldihydropyrans were obtained in high yields and with up to 95% ee within a short reaction time. A useful transformation of the chiral adduct was also illustrated.

引用

页码：7369 / 7371

页数：3

共 51 条

[1] Novel bifunctional chiral urea and thiourea derivatives as organocatalysts:: Enantioselective nitro-Michael reaction of malonates and diketones [J].