文献类型：期刊文献

英文题名：Stereoselective organocatalytic oxidation of alcohols to enals: a homologation method to prepare polyenes

作者：Chen, Xiaobei[1,2,3];Zhang, Yinan[4];Wan, Huixin[5];Wang, Wei[3,4];Zhang, Shilei[1,2]

机构：[1]Soochow Univ, Coll Pharmaceut Sci, Jiangsu Key Lab Translat Res & Therapy Neuropsych, 199 Renai Rd, Suzhou 215123, Peoples R China;[2]Soochow Univ, Coll Pharmaceut Sci, Dept Med Chem, 199 Renai Rd, Suzhou 215123, Peoples R China;[3]E China Univ Sci & Technol, Sch Pharm, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[4]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA;[5]Shanghai Pharmaceut Holding Co Ltd, Cent Res Inst, Tower 4,898 Ha Lei Rd, Shanghai 201203, Peoples R China

年份：2016

卷号：52

期号：17

起止页码：3532

外文期刊名：CHEMICAL COMMUNICATIONS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000371026700018)，CCR-EXPANDED(收录号:WOS:000371026700018)】；

基金：This work was supported by the National Natural Science Foundation of China (Grant No. 21202112) and PAPD (a project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions).

语种：英文

摘要：A novel method for organocatalytic oxidation through oxidative enamine catalysis was developed with excellent compatibility for the direct syntheses of enals from simple saturated alcohols. By using this amine-catalyzed IBX-oxidation, a wide range of aromatic and aliphatic substituted enals were successfully generated in high yields and exclusively stereoselective E-geometry. Moreover, varying the solvents and/or the loading amounts of IBX allowed for the selective oxidation of alcohols and aldehydes. Importantly, the homologous application of this method provided a selective and efficient way of preparing various highly sensitive conjugated polyene frameworks, which are enriched in natural products.