Synthesis 2020; 52(09): 1387-1397
DOI: 10.1055/s-0039-1691597
paper
© Georg Thieme Verlag Stuttgart · New York

1,3-Dipolar Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and O-Vinylphosphonylated Salicylaldehydes for Diastereoselective Synthesis of Oxindole Spiro-P,N-polycyclic Heterocycles

Authors

  • Tiao Huang

    a   Key Laboratory of Tropical Medicinal Resource Chemistry of the Ministry of Education, Hainan Normal University, Haikou 571158, P. R. of China   eMail: wmsh@hainnu.edu.cn
  • Li Liu

    a   Key Laboratory of Tropical Medicinal Resource Chemistry of the Ministry of Education, Hainan Normal University, Haikou 571158, P. R. of China   eMail: wmsh@hainnu.edu.cn
  • Qinghe Wang

    a   Key Laboratory of Tropical Medicinal Resource Chemistry of the Ministry of Education, Hainan Normal University, Haikou 571158, P. R. of China   eMail: wmsh@hainnu.edu.cn
  • Mingshu Wu

    a   Key Laboratory of Tropical Medicinal Resource Chemistry of the Ministry of Education, Hainan Normal University, Haikou 571158, P. R. of China   eMail: wmsh@hainnu.edu.cn
  • Dulin Kong

    b   School of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, Hainan Province, P. R. of China

We gratefully acknowledge the financial support from Program of Natural Science Foundation of Hainan Province (2019RC215) and Graduate Innovative Research Project of Hainan Normal University (Hsyx2018-25).
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Publikationsverlauf

Received: 04. November 2019

Accepted after revision: 21. Januar 2020

Publikationsdatum:
12. Februar 2020 (online)


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Abstract

An efficient stereoselective assembly strategy for the construction of pyrrolidin-2,3′-oxindole cis-fused phosphadihydrocoumarins was established. The process involves the condensation of O-vinylphosphonylated salicylaldehydes and 3-amino oxindoles followed by intermolecular cycloaddition with high diastereoselectivity and atom economy.

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