有机化学 ›› 2018, Vol. 38 ›› Issue (12): 3373-3380.DOI: 10.6023/cjoc201806010 上一篇    下一篇

研究简报

不对称有机催化构筑二环己内酰胺类化合物

张雄a, 封凯祥b, 夏爱宝b   

  1. a 浙江外国语学院 科学技术学院 杭州 310023;
    b 浙江工业大学催化加氢研究中心 浙江省绿色农药清洁生产技术研究重点实验室 杭州 310014
  • 收稿日期:2018-06-07 修回日期:2018-08-20 出版日期:2018-12-25 发布日期:2018-09-05
  • 通讯作者: 张雄, 夏爱宝 E-mail:xiongzhang1212@126.com;xiaaibao@zjut.edu.cn
  • 基金资助:

    浙江省自然科学基金(No.LY18B020017)资助项目.

Asymmetric Organocatalytic Construction of Functionalized Bicyclic Lactams

Zhang Xionga, Feng Kaixiangb, Xia Aibaob   

  1. a School of Science & Technology, Zhejiang International Studies University, Hangzhou 310023;
    b Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Catalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014
  • Received:2018-06-07 Revised:2018-08-20 Online:2018-12-25 Published:2018-09-05
  • Contact: 10.6023/cjoc201806010 E-mail:xiongzhang1212@126.com;xiaaibao@zjut.edu.cn
  • Supported by:

    Project supported by the Natural Science Foundation of Zhejiang Province (No. LY18B020017).

设计了一例αβ-不饱和烯醛与含有双亲核活性中心的α-酮酰胺不对称有机催化高选择性的Michael-hemiamina-lization-hemiacetalization串联反应,并以高收率(up to 97%)、优异的对映选择性和非对映选择性(up to > 99% ee,>20:1 dr)获得一系列具有两个顺式手性中心的二环己内酰胺化合物.

关键词: 不对称合成, Michael-hemiaminalization-hemiacetalization反应, 二环己内酰胺

A novel enantioselective organocatalytic cascade Michael-hemiaminalization-hemiacetalization reaction of α,β-unsaturated aldehydes with α-ketoamides as binucleophiles has been developed. A series of chiral functionalized bicyclic lactams with two cis contiguous stereogenic centers have been synthesized in up to 97% yield with up to >20:1 dr and up to >99% ee.

Key words: asymmetric synthesis, Michael-hemiaminalization-hemiacetalization reaction, bicyclic lactam