Synlett 2022; 33(19): 1873-1878
DOI: 10.1055/a-1904-0582
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Catalytic Asymmetric [3+3] Cycloaddition of Activated Isocyanides with Azomethine Imines

Ling-Fei Tao
a   College of Pharmaceutical Sciences, and Hangzhou Institute of Innovative Medicine, Zhejiang University, Hangzhou, 310058, P. R. of China
,
Linghui Qian
a   College of Pharmaceutical Sciences, and Hangzhou Institute of Innovative Medicine, Zhejiang University, Hangzhou, 310058, P. R. of China
,
Jia-Yu Liao
a   College of Pharmaceutical Sciences, and Hangzhou Institute of Innovative Medicine, Zhejiang University, Hangzhou, 310058, P. R. of China
b   Innovation Institute for Artificial Intelligence in Medicine of Zhejiang University, Hangzhou, 310018, P. R. of China
› Institutsangaben
The authors acknowledge financial support from the National Natural Science Foundation of China (81903574), the Fundamental Research Funds for the Central Universities (2020QNA7001), and Zhejiang University.


In memory of Professor Rolf Huisgen

Abstract

Catalytic asymmetric 1,3-dipolar cycloaddition reactions of activated isocyanides with various 2π dipolarophiles have been intensively studied, affording a wide range of enantioenriched five-membered N-heterocycles. In sharp contrast, the catalytic enantioselective higher-order cycloaddition of activated isocyanides has not been achieved yet. We present here our recent work on the development of an unprecedented silver-catalyzed highly diastereo- and enantioselective [3+3] cycloaddition of activated isocyanides with azomethine imines. This method features high efficiency, good to excellent stereocontrol, wide substrate scope, as well as operational simplicity. It is also noteworthy that the same catalytic system was proved to be suitable for not only the late-stage functionalization of complex bioactive molecules but also the kinetic resolution of racemic azomethine imines.

1 Introduction

2 Results and Discussion

3 Summary and Outlook



Publikationsverlauf

Eingereicht: 06. Juli 2022

Angenommen nach Revision: 19. Juli 2022

Accepted Manuscript online:
19. Juli 2022

Artikel online veröffentlicht:
12. August 2022

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