3 years ago

Organocatalyzed Asymmetric Vinylogous Addition of Oxazole-2(3H)-thiones to α,β-Unsaturated Ketones: An Additive-Free Approach for Diversification of Heterocyclic Scaffold

Organocatalyzed Asymmetric
Vinylogous Addition of
Oxazole-2(3H)-thiones to α,β-Unsaturated
Ketones: An Additive-Free Approach for Diversification of Heterocyclic
Scaffold
Julio Zukerman-Schpector, Márcio W. Paixão, Lucas V. Pozzi, Marco A. B. Ferreira, Sandrina Silva, Rodrigo C. da Silva, Patrick Rollin, Arlene G. Correa, Bianca T. Matsuo
A straightforward organocatalyzed asymmetric addition of oxazole-2(3H)-thiones to α,β-unsaturated ketones is described. This additive-free Michael reaction in the presence of chiral cinchonine-derived primary amines as catalysts has proven to be highly effective for a wide range of cyclic and acyclic enones, leading to the Michael adducts in very good yields and excellent enantioselectivities. The absolute configuration (R) of compound 5j was unambiguously assigned by X-ray diffraction analysis. Furthermore, experimental and theoretical studies were performed and a mechanism is presented and discussed for this novel reaction.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02236

DOI: 10.1021/acs.joc.7b02236

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