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Zhang B, Han F, Wang L, et al. Catalytic Asymmetric Michael Reaction of 5H-Oxazol-4-Ones with α,β-Unsaturated Acyl Imidazoles. Chemistry. 2015;21(48):17234-8doi: 10.1002/chem.201503105.
Zhang, B., Han, F., Wang, L., Li, D., Yang, D., Yang, X., Yang, J., Li, X., Zhao, D., & Wang, R. (2015). Catalytic Asymmetric Michael Reaction of 5H-Oxazol-4-Ones with α,β-Unsaturated Acyl Imidazoles. Chemistry (Weinheim an der Bergstrasse, Germany), 21(48), 17234-8. https://doi.org/10.1002/chem.201503105
Zhang, Bangzhi, et al. "Catalytic Asymmetric Michael Reaction of 5H-Oxazol-4-Ones with α,β-Unsaturated Acyl Imidazoles." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,48 (2015): 17234-8. doi: https://doi.org/10.1002/chem.201503105
Zhang B, Han F, Wang L, Li D, Yang D, Yang X, Yang J, Li X, Zhao D, Wang R. Catalytic Asymmetric Michael Reaction of 5H-Oxazol-4-Ones with α,β-Unsaturated Acyl Imidazoles. Chemistry. 2015 Nov 23;21(48):17234-8. doi: 10.1002/chem.201503105. Epub 2015 Oct 14. PMID: 26439322.
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Chemistry. 2015 Nov 23;21(48):17234-8. doi: 10.1002/chem.201503105. Epub 2015 Oct 14.

Catalytic Asymmetric Michael Reaction of 5H-Oxazol-4-Ones with α,β-Unsaturated Acyl Imidazoles.

Chemistry (Weinheim an der Bergstrasse, Germany)

Bangzhi Zhang, Fengxia Han, Linqing Wang, Dan Li, Dongxu Yang, Xiaoli Yang, Junxian Yang, Xiaofang Li, Depeng Zhao, Rui Wang

Affiliations

  1. School of Life Sciences, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (China).
  2. School of Life Sciences, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (China). [email protected].

PMID: 26439322 DOI: 10.1002/chem.201503105

Abstract

The asymmetric Michael reaction between 5H-oxazol-4-ones and α,β-unsaturated acyl imidazoles is reported. A novel 2-benzo[b]thiophenyl-modified chiral ProPhenol species is synthesized and used as a ligand, leading to good enantioselectivities in this asymmetric conjugate addition reaction. Furthermore, the introduction of phenol additives as achiral co-ligands is found to improve the reaction's chemical yields, diastereoselectivities, and enantioselectivities.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Michael addition; asymmetric synthesis; heterocycles; ligand design; zinc

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