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Hang Z, Zhu J, Lian X, et al. A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines. Chem Commun (Camb). 2016;52(1):80-3doi: 10.1039/c5cc07880f.
Hang, Z., Zhu, J., Lian, X., Xu, P., Yu, H., & Han, S. (2016). A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines. Chemical communications (Cambridge, England), 52(1), 80-3. https://doi.org/10.1039/c5cc07880f
Hang, Zhijun, et al. "A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines." Chemical communications (Cambridge, England) vol. 52,1 (2016): 80-3. doi: https://doi.org/10.1039/c5cc07880f
Hang Z, Zhu J, Lian X, Xu P, Yu H, Han S. A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines. Chem Commun (Camb). 2016 Jan 04;52(1):80-3. doi: 10.1039/c5cc07880f. PMID: 26498376.
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Chem Commun (Camb). 2016 Jan 04;52(1):80-3. doi: 10.1039/c5cc07880f.

A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines.

Chemical communications (Cambridge, England)

Zhijun Hang, Jun Zhu, Xiang Lian, Peng Xu, Han Yu, Sheng Han

Affiliations

  1. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. China. [email protected] [email protected].
  2. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. China. [email protected] [email protected] and Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.

PMID: 26498376 DOI: 10.1039/c5cc07880f

Abstract

An efficient self-assembled methanoproline-thiourea organocatalyst for the synthesis of optically active 6-isopropyl-3,4-dihydro-pyrimidines via an asymmetric Biginelli reaction was developed, which is superior to the individual precatalyst. A wide range of optically active 6-isopropyl-3,4-dihydropyrimidines with remarkable pharmacological interest was obtained in high yields with excellent enantioselectivities (up to 99% ee). A plausible transition state has been proposed to explain the origin of the activation and the asymmetric induction.

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