Diastereoselective Synthesis of Dispirobarbiturates through Et3N‑Catalyzed [3 + 2] Cycloaddition of Barbiturate-Based Olefins with 3‑Isothiocyanato Oxindoles
Under catalysis of 10 mol % of Et3N, the [3 + 2] cycloaddition of barbiturate-based olefins with 3-isothiocyanato oxindoles underwent smoothly and afforded the desired dispirobarbiturates in up to 99% yield with up to 99:1 dr. The relative configuration of the dispirobarbiturates was unambiguously d...
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Veröffentlicht in: | Journal of organic chemistry 2015-10, Vol.80 (20), p.10380-10385 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | Under catalysis of 10 mol % of Et3N, the [3 + 2] cycloaddition of barbiturate-based olefins with 3-isothiocyanato oxindoles underwent smoothly and afforded the desired dispirobarbiturates in up to 99% yield with up to 99:1 dr. The relative configuration of the dispirobarbiturates was unambiguously determined by X-ray single-crystal structure analysis. The reaction mechanism was proposed to shed light on the diastereoselective formation of the dispirobarbiturates. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.5b01810 |