有机化学 ›› 2018, Vol. 38 ›› Issue (3): 672-676.DOI: 10.6023/cjoc201710004 上一篇    下一篇

研究论文

(S)-联萘酚钛体系催化3-噻吩铝试剂对酮的不对称加成反应

戈敏, 张丽军, 涂兵, 周双六   

  1. 功能分子固体教育部重点实验室 分子基材料安徽省重点实验室安徽师范大学化学与材料科学学院 芜湖 241000
  • 收稿日期:2017-10-07 修回日期:2017-11-09 出版日期:2018-03-25 发布日期:2017-11-17
  • 通讯作者: 张丽军,E-mail:zljun@mail.ahnu.edu.cn;周双六,E-mail:slzhou@ahnu.edu.cn E-mail:zljun@mail.ahnu.edu.cn;slzhou@ahnu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21372009,21672004)资助项目.

Asymmetric Addition of 3-Thienyl Aluminum to Ketones Catalyzed by the Simple Titanium Catalytic System of (S)-1,1'-Binaphthol

Ge Min, Zhang Lijun, Tu Bing, Zhou Shuangliu   

  1. Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000
  • Received:2017-10-07 Revised:2017-11-09 Online:2018-03-25 Published:2017-11-17
  • Contact: 10.6023/cjoc201710004 E-mail:zljun@mail.ahnu.edu.cn;slzhou@ahnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21372009, 21672004).

含噻吩基团的的手性芳香醇是自然界重要的活性物质,其基本结构单元广泛地存在于生物活性物质和医药中.报道了(S)-联萘酚和Ti(OiPr)4催化3-噻吩基铝试剂对酮的不对称加成反应,以较高的产率和优异的立体选择性(高达91%ee)得到相应的含有3-噻吩基乙醇.该催化体系具有广泛的适应性,能够适合含有吸电子和供电子基团的各种酮的不对称加成,得到相应的3-噻吩基乙醇.

关键词: 不对称合成, 噻吩基, 铝试剂, 钛,

The optically active diaryl alcohols bearing thienyl group are well-known for their biological activity as well as key substructure in bioactive compounds and pharmaceuticals. The asymmetric addition of 3-thienyl aluminum to ketones afforded the optically active 3-thienyl arylethanols in good yields with high enantioselectivities of up to 91% ee employing the simple titanium catalytic system of (S)-1,1'-binaphthol. The catalytic system could also suit for various ketones bearing an electron-donating or electron-withdrawing groups to afford the corresponding diarylethanols containing substituted 3-thienyl groups.

Key words: asymmetric synthesis, thienyl, aluminum, titanium, ketones