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Primary amine catalyzed diastereo- and enantioselective Michael reaction of thiazolones and α,β-unsaturated ketones

Abstract

The chiral primary amine catalyzed asymmetric Michael reaction of thiazolones and α,β-unsaturated ketones was reported. Two different optimal catalytic systems were obtained responding to cyclic and linear α,β-unsaturated ketones. By employing chiral primary amine as the catalyst and amino-acid derivative as the additive, a variety of Michael adducts containing the scaffold of thiazole ring were prepared with moderate to good yields, excellent diastereo- and enantioselectivities (up to 95% yield, all up to >19/1 dr, up to 96% ee). The reaction was scaled up to obtain 1.73 grams of the Michael adduct with the maintenance of yield and stereoselectivity

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Publication details

The article was received on 23 Sep 2019, accepted on 11 Oct 2019 and first published on 11 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB02067E
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Primary amine catalyzed diastereo- and enantioselective Michael reaction of thiazolones and α,β-unsaturated ketones

    M. Lu, H. Li, C. Zou, J. Li, C. Liu, M. Sun, Y. Ma, R. Cheng and J. Ye, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB02067E

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