Selective synthesis of iminodioxaspirononanes and diazaspirononanes using formic acid-activated Mn(III) oxidation of N1,N3-disubstitued malonamides with 1,1-diarylethenes

Selective synthesis of iminodioxaspirononanes and diazaspirononanes using formic acid-activated Mn(III) oxidation of N1,N3-disubstitued malonamides with 1,1-diarylethenes

The Mn(III)-based oxidation of N1,N3-disubstituted malonamides with alkenes by Kurosawa spirolactonization using malonic acid afforded iminodihydrofurans. A similar reaction with Mn(OAc)3, which was activated by HCO2H, selectively gave iminodioxaspirononanes at room temperature and diazaspirononanes...

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Veröffentlicht in:Tetrahedron 2022-01, Vol.105, p.132611, Article 132611
Hauptverfasser: Shimoishi, Ryutaro, Nakano, Yûki, Wada, Ryosei, El-Deeb, Ibrahim Yussif, Nishino, Hiroshi
Format: Artikel
Sprache:eng
Schlagworte:
Diazaspirononanes
Dioxaspirodiimines
Formic acid-activated Mn(III)-based oxidation
Iminodihydrofurans
Iminodioxaspirononanes
Selective synthesis
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Zusammenfassung:The Mn(III)-based oxidation of N1,N3-disubstituted malonamides with alkenes by Kurosawa spirolactonization using malonic acid afforded iminodihydrofurans. A similar reaction with Mn(OAc)3, which was activated by HCO2H, selectively gave iminodioxaspirononanes at room temperature and diazaspirononanes at reflux temperature. The mechanism for the formation of the products including intermediate byproducts is discussed. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2021.132611