A Full Regioselective and Stereoselective Synthesis of 4‐Nitroisoxazolidines via Stepwise [3 + 2] Cycloaddition Reactions between (Z)‐C‐(9‐Anthryl)‐N‐arylnitrones and (E)‐3,3,3‐Trichloro‐1‐nitroprop‐1‐ene: Comprehensive Experimental and Theoretical Study

In the contrast to all known [3 + 2] cycloadditions between nitrones and conjugated nitroalkenes, reactions of (E)‐3,3,3‐trichloro‐1‐nitroprop‐1‐ene with (Z)‐C‐(9‐anthryl)‐N‐arylnitrones are proceeding in a fully regioselective and stereoselective manner. Additionally, density functional theory calc...

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Veröffentlicht in:Journal of heterocyclic chemistry 2017-11, Vol.54 (6), p.3314-3320
Hauptverfasser: Jasiński, Radomir, Żmigrodzka, Magdalena, Dresler, Ewa, Kula, Karolina
Format: Artikel
Sprache:eng
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Zusammenfassung:In the contrast to all known [3 + 2] cycloadditions between nitrones and conjugated nitroalkenes, reactions of (E)‐3,3,3‐trichloro‐1‐nitroprop‐1‐ene with (Z)‐C‐(9‐anthryl)‐N‐arylnitrones are proceeding in a fully regioselective and stereoselective manner. Additionally, density functional theory calculations suggest stepwise, zwitterionic mechanism of these cycloadditions.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.2951