Diastereoselective construction of a library of structural bispiro[butyrolactone/valerolactone–pyrrolidine–indanedione] hybrids via 1,3-dipolar cycloaddition reactions

Herein, a highly efficient strategy that allows the diverse synthesis of a library of structural bispiro[butyrolactone–pyrrolidine–indanedione] hybrids is achieved effectively for the first time by means of 1,3-dipolar cycloadditions of α,β-unsaturated butyrolactones/valerolactones as dipolarophiles...

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Bibliographic Details
Published in:New journal of chemistry 2022-06, Vol.46 (25), p.11975-11979
Main Authors: Zhang, Lei, Quan, Wei, Liu, Ren-Ming, Tian, You-Ping, Pan, Bo-Wen, Liu, Xiong-Li
Format: Article
Language:English
Subjects:
Butyrolactone
Cycloaddition
Libraries
Ninhydrin
Stereoselectivity
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Summary:Herein, a highly efficient strategy that allows the diverse synthesis of a library of structural bispiro[butyrolactone–pyrrolidine–indanedione] hybrids is achieved effectively for the first time by means of 1,3-dipolar cycloadditions of α,β-unsaturated butyrolactones/valerolactones as dipolarophiles with azomethine ylides (thermally generated in situ from ninhydrin and proline or thioproline) via an exo′-transition state. Potentially bioactive target compounds have been obtained in good yields and diastereoselectivities (up to 89% yield and all cases >20 : 1 dr).
ISSN:1144-0546
1369-9261
DOI:10.1039/D2NJ01571D