靛红 N,N'-环亚甲胺基叶立德与马来酰亚胺的异常 [3 + 2]-环加成反应在 1,4-二氮杂二环[2.2.2]辛烷存在下的研究
Isatin N,N'-Cyclic Azomethine Imine 1,3-Dipole and Abnormal [3 + 2]-Cycloaddition with Maleimide in the Presence of 1,4-Diazabicyclo[2.2.2]octane.
机构信息
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.
University of Chinese Academy of Sciences , Beijing 100049, China.
出版信息
Org Lett. 2017 Feb 3;19(3):646-649. doi: 10.1021/acs.orglett.6b03815. Epub 2017 Jan 23.
A new isatin N,N'-cyclic azomethine imine synthon was devised, and an unexpected abnormal [3 + 2]-cycloaddition with maleimide catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) has been disclosed. A variety of tricyclic spiropyrrolidine oxindoles bearing a dinitrogen heterocycle and succinimide scaffold were obtained in excellent yields (up to 96%) and diastereoselectivities (up to 97:3) under mild conditions.
设计了一种新的靛红 N,N'-环亚氨基席夫碱合成子，并揭示了在 1,4-二氮杂二环[2.2.2]辛烷（DABCO）催化下马来酰亚胺与它的异常[3+2]-环加成反应。在温和条件下，以优异的收率（高达 96%）和非对映选择性（高达 97:3）得到了多种含有二氮杂环戊烷和琥珀酰亚胺支架的三环螺吡咯烷吲哚酮。
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