Access to (Z)‑β-Substituted Enamides from N1‑H-1,2,3-Triazoles

A direct ring-opening/nucleophilic substitution reaction of N1-H-1,2,3-triazoles has been described. Divergent (Z)-β-halogen- or sulfonyl-substituted enamides could be stereospecifically synthesized in a tunable manner. This strategy might not only enable a new ring-opening method of N1-H-1,2,3-tria...

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Veröffentlicht in:Organic letters 2021-08, Vol.23 (16), p.6293-6298
Hauptverfasser: Wang, Tao, Tang, Zongyuan, Luo, Han, Tian, Yi, Xu, Mingchuan, Lu, Qixing, Li, Baosheng
Format: Artikel
Sprache:eng
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Zusammenfassung:A direct ring-opening/nucleophilic substitution reaction of N1-H-1,2,3-triazoles has been described. Divergent (Z)-β-halogen- or sulfonyl-substituted enamides could be stereospecifically synthesized in a tunable manner. This strategy might not only enable a new ring-opening method of N1-H-1,2,3-triazoles under nonmetal catalysis and mild reaction conditions but also offer a good opportunity to reliably access versatile (Z)-β-substituted enamides that could be used as synthetic precursors for further synthetic transformations.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02087