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
Hauptverfasser: Zhao, Hong-Wu, Tian, Ting, Li, Bo, Yang, Zhao, Pang, Hai-Liang, Meng, Wei, Song, Xiu-Qing, Chen, Xiao-Qin
Format: Artikel
Sprache:eng
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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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01810