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Zhao HW, Tian T, Li B, et al. Diastereoselective Synthesis of Dispirobarbiturates through Et3N-Catalyzed [3 + 2] Cycloaddition of Barbiturate-Based Olefins with 3-Isothiocyanato Oxindoles. J Org Chem. 2015;80(20):10380-5doi: 10.1021/acs.joc.5b01810.
Zhao, H. W., Tian, T., Li, B., Yang, Z., Pang, H. L., Meng, W., Song, X. Q., & Chen, X. Q. (2015). Diastereoselective Synthesis of Dispirobarbiturates through Et3N-Catalyzed [3 + 2] Cycloaddition of Barbiturate-Based Olefins with 3-Isothiocyanato Oxindoles. The Journal of organic chemistry, 80(20), 10380-5. https://doi.org/10.1021/acs.joc.5b01810
Zhao, Hong-Wu, et al. "Diastereoselective Synthesis of Dispirobarbiturates through Et3N-Catalyzed [3 + 2] Cycloaddition of Barbiturate-Based Olefins with 3-Isothiocyanato Oxindoles." The Journal of organic chemistry vol. 80,20 (2015): 10380-5. doi: https://doi.org/10.1021/acs.joc.5b01810
Zhao HW, Tian T, Li B, Yang Z, Pang HL, Meng W, Song XQ, Chen XQ. Diastereoselective Synthesis of Dispirobarbiturates through Et3N-Catalyzed [3 + 2] Cycloaddition of Barbiturate-Based Olefins with 3-Isothiocyanato Oxindoles. J Org Chem. 2015 Oct 16;80(20):10380-5. doi: 10.1021/acs.joc.5b01810. Epub 2015 Oct 07. PMID: 26402054.
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J Org Chem. 2015 Oct 16;80(20):10380-5. doi: 10.1021/acs.joc.5b01810. Epub 2015 Oct 07.

Diastereoselective Synthesis of Dispirobarbiturates through Et3N-Catalyzed [3 + 2] Cycloaddition of Barbiturate-Based Olefins with 3-Isothiocyanato Oxindoles.

The Journal of organic chemistry

Hong-Wu Zhao, Ting Tian, Bo Li, Zhao Yang, Hai-Liang Pang, Wei Meng, Xiu-Qing Song, Xiao-Qin Chen

Affiliations

  1. College of Life Science and Bio-engineering, Beijing University of Technology , Beijing 100124, P. R. China.

PMID: 26402054 DOI: 10.1021/acs.joc.5b01810

Abstract

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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