Synthesis of pyrrolidin-2-ylidenes and pyrrol-2-ylidenes <i>via</i> 1,3-dipolar cycloaddition of H-bond-assisted azomethine ylides to nitrostyrenes

Yavari, Issa; Mohsenzadeh, Ramin; Ravaghi, Parisa; Safaei, Maryam

doi:10.1039/d3ob00725a

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Reaction With In Situ Prepared Azomethine Ylides1

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2024

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Cited by 4 publications

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“…The bromine in 113 is removed by the attack of a cyanide ion followed by protonation to give the final 2-pyrrolidinylidene product 109 (Scheme 41). 43…”

Section: Reaction With In Situ Prepared Azomethine Ylidesmentioning

confidence: 99%

Bromonitroalkenes as efficient intermediates in organic synthesis

Ziyaei Halimehjani,

Tahvildari

2024

Org. Biomol. Chem.

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“…The bromine in 113 is removed by the attack of a cyanide ion followed by protonation to give the final 2-pyrrolidinylidene product 109 (Scheme 41). 43…”

Section: Reaction With In Situ Prepared Azomethine Ylidesmentioning

confidence: 99%

Bromonitroalkenes as efficient intermediates in organic synthesis

Ziyaei Halimehjani,

Tahvildari

2024

Org. Biomol. Chem.

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Diastereoselective Synthesis of NH-Unprotected Spiropyrrolidines via the Huisgen Reaction of Acenaphthoquinone-Derived Azomethine Ylides with β-Nitrostyrenes

Yavari,

Ghafouri

2024

Synthesis

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Abstract4′-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.

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