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DOI: 10.1055/s-0042-1751581
Diastereoselective Synthesis of NH-Unprotected Spiropyrrolidines via the Huisgen Reaction of Acenaphthoquinone-Derived Azomethine Ylides with β-Nitrostyrenes
We are grateful to the Research Council of Tarbiat Modares University for support of this work.
Abstract
4′-Nitro-2H-spiro[acenaphthylene-1,2′-pyrrolidine]-2-one derivatives are prepared via [3+2] cycloaddition reactions of azomethine ylides, generated in situ from acenaphthoquinone and primary amines, with β-nitrostyrenes in the presence of ( i Pr)2NEt in methanol. Evidence for the structures of the products was obtained from single-crystal X-ray analysis. The important feature of this diastereoselective synthesis of NH-unprotected spiropyrrolidines is the formation of four contiguous stereogenic centers, one of which is quaternary, with high selectivity.
Key words
azomethine ylide - Huisgen reaction - spiro compound - β-nitrostyrenes - acenaphthoquinoneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751581.
- Supporting Information
Publication History
Received: 29 January 2024
Accepted after revision: 20 March 2024
Article published online:
04 April 2024
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