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

Xiao Wang; Peng Yang; Yong Zhang; Chao-Zhe Tang; Fang Tian; Lin Peng; Li-Xin Wang

doi:10.1021/acs.orglett.6b03815

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

Org Lett. 2017 Feb 3;19(3):646-649. doi: 10.1021/acs.orglett.6b03815. Epub 2017 Jan 23.

Authors

Xiao Wang^{1

2}, Peng Yang^{1

2}, Yong Zhang^{1

2}, Chao-Zhe Tang^{1

2}, Fang Tian¹, Lin Peng¹, Li-Xin Wang¹

Affiliations

¹ Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.
² University of Chinese Academy of Sciences , Beijing 100049, China.

PMID: 28111956
DOI: 10.1021/acs.orglett.6b03815

Abstract

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.