Chiral Spirooxindole–Butenolide Synthesis through Asymmetric N‑Heterocyclic Carbene-Catalyzed Formal (3 + 2) Annulation of 3‑Bromoenals and Isatins

Chiral Spirooxindole–Butenolide Synthesis through Asymmetric N‑Heterocyclic Carbene-Catalyzed Formal (3 + 2) Annulation of 3‑Bromoenals and Isatins

By using an N-heterocyclic carbene catalyst bearing a hydroxyl moiety, the asymmetric formal (3 + 2) cyclization of aryl 3-bromoenals and isatins was achieved to produce a series of chiral spirooxindole–butenolides including an alkenyl-substituted compound, which underwent benzannulations with benzy...

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Veröffentlicht in:Organic letters 2014-10, Vol.16 (19), p.5028-5031
Hauptverfasser: Zheng, Chenguang, Yao, Weijun, Zhang, Yucheng, Ma, Cheng
Format: Artikel
Sprache:eng
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Zusammenfassung:By using an N-heterocyclic carbene catalyst bearing a hydroxyl moiety, the asymmetric formal (3 + 2) cyclization of aryl 3-bromoenals and isatins was achieved to produce a series of chiral spirooxindole–butenolides including an alkenyl-substituted compound, which underwent benzannulations with benzynes to form intriguing spirocyclic scaffolds.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502365r