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

Org Biomol Chem 2019 10;17(42):9305-9312

Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.

The chiral primary amine catalyzed asymmetric Michael reaction of thiazolones and α,β-unsaturated ketones was reported. Two different optimal catalytic systems were obtained corresponding to cyclic and linear α,β-unsaturated ketones. By employing chiral primary amines as the catalysts and amino-acid derivatives as the additives, a variety of Michael adducts containing the scaffold of the thiazole ring were prepared in moderate to good yields and with 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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http://dx.doi.org/10.1039/c9ob02067eDOI Listing
October 2019

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References

(Supplied by CrossRef)

Siddiqui et al.
Int. J. Pharm. Sci. Drug Res. 2009

Venkatesh et al.
Int. J. ChemTech Res. 2009

Gupta et al.
J. Chem. Pharm. Res. 2010

Nagararaju et al.
Indo Am. J. Pharm. Res. 2015

Eleftheriou et al.
Eur. J. Med. Chem. 2012

Azam et al.
Sci. Pharm. 2012

Desai et al.
J. Saudi Chem. Soc. 2016

Ahmed et al.
Molecules 2016

Gjorgjieva et al.
J. Med. Chem. 2016

Yusufzai et al.
Chem. Cent. J. 2018

Liaras et al.
Molecules 2018

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