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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
› Author AffiliationsThe 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.
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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

Key words

heterocycles - cycloaddition - kinetic resolution - diastereoselectivity - enantioselectivity


Publication History

Received: 06 July 2022

Accepted after revision: 19 July 2022

Accepted Manuscript online:
19 July 2022

Article published online:
12 August 2022

© 2022. Thieme. All rights reserved

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