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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 *
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
* Author to whom correspondence should be addressed.
Received: 13 October 2010 / Revised: 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 (CC BY 3.0).

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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.

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