Synthesis of spiropyrrolidine oxindoles through Rh(II)-catalyzed olefination/cyclization of diazooxindoles and vinyl azides

doi:10.1016/S1872-2067(18)63200-0

Chinese Journal of Catalysis ›› 2019, Vol. 40 ›› Issue (2): 177-183.DOI: 10.1016/S1872-2067(18)63200-0

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Synthesis of spiropyrrolidine oxindoles through Rh(II)-catalyzed olefination/cyclization of diazooxindoles and vinyl azides

Ruxia Yi^a,b, Leilei Qian^a,b, Boshun Wan^a

a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

Received:2018-11-02 Revised:2018-11-14 Online:2019-02-28 Published:2019-01-11
Contact: 10.1016/S1872-2067(18)63200-0
Supported by:
This work was supported by the National Natural Science Foundation of China (21572225).

Abstract

Abstract:

A simple and efficient process involving the Rh(Ⅱ)-catalyzed[1+1+3] annulation of diazooxindoles and vinyl azides has been developed for the synthesis of spiropyrrolidine oxindoles with potential biological activity and significant synthetic applications. This process involves a novel rhodium-catalyzed olefination of diazo compounds, followed by annulation with vinyl azides. This method is compatible with a broad range of substrates and affords moderate to good yields under mild reaction conditions.

Key words: Rhodium catalyst, Vinyl azides, Diazo compounds, Spiropyrrolidine oxindoles, Olefination, [1+1+3] annulation

Ruxia Yi, Leilei Qian, Boshun Wan. Synthesis of spiropyrrolidine oxindoles through Rh(II)-catalyzed olefination/cyclization of diazooxindoles and vinyl azides[J]. Chinese Journal of Catalysis, 2019, 40(2): 177-183.

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Synthesis of spiropyrrolidine oxindoles through Rh(II)-catalyzed olefination/cyclization of diazooxindoles and vinyl azides

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