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Molecules 2010, 15(11), 8305-8326; doi:10.3390/molecules15118305
Article

Catalytic Asymmetric Synthesis of Both Enantiomers of 4‑Substituted 1,4-Dihydropyridines with the Use of Bifunctional Thiourea-Ammonium Salts Bearing Different Counterions

, ,  and *
Received: 13 October 2010; in revised form: 8 November 2010 / Accepted: 12 November 2010 / Published: 15 November 2010
(This article belongs to the Special Issue Bifunctional Catalysis)
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Abstract: Organoammonium salts composed of a Brønsted acid and an anilinothiourea promoted the Michael addition of β-keto esters and α,β-unsaturated aldehydes in the presence of primary amines to give functionalized 1,4-dihydropyridines enantioselectively. With the use of the different Brønsted acids such as DFA and HBF4 with the same bifunctional thiourea, both enantiomers of 4-substituted 1,4-dihydropyridine were synthesized from the same starting materials.
Keywords: bifunctional thiourea-ammonium salt; aminothiourea; Brønsted acid; 1,4-dihydropyridines; Michael addition; a,b-unsaturated aldehydes; b-keto esters bifunctional thiourea-ammonium salt; aminothiourea; Brønsted acid; 1,4-dihydropyridines; Michael addition; a,b-unsaturated aldehydes; b-keto esters
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Yoshida, K.; Inokuma, T.; Takasu, K.; Takemoto, Y. Catalytic Asymmetric Synthesis of Both Enantiomers of 4‑Substituted 1,4-Dihydropyridines with the Use of Bifunctional Thiourea-Ammonium Salts Bearing Different Counterions. Molecules 2010, 15, 8305-8326.

AMA Style

Yoshida K, Inokuma T, Takasu K, Takemoto Y. Catalytic Asymmetric Synthesis of Both Enantiomers of 4‑Substituted 1,4-Dihydropyridines with the Use of Bifunctional Thiourea-Ammonium Salts Bearing Different Counterions. Molecules. 2010; 15(11):8305-8326.

Chicago/Turabian Style

Yoshida, Kohzo; Inokuma, Tsubasa; Takasu, Kiyosei; Takemoto, Yoshiji. 2010. "Catalytic Asymmetric Synthesis of Both Enantiomers of 4‑Substituted 1,4-Dihydropyridines with the Use of Bifunctional Thiourea-Ammonium Salts Bearing Different Counterions." Molecules 15, no. 11: 8305-8326.


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