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. 2010 Nov 15;15(11):8305-26.
doi: 10.3390/molecules15118305.

Catalytic asymmetric synthesis of both enantiomers of 4‑substituted 1,4-dihydropyridines with the use of bifunctional thiourea-ammonium salts bearing different counterions

Kohzo Yoshida  1 , Tsubasa Inokuma, Kiyosei Takasu, Yoshiji Takemoto
Affiliations

Catalytic asymmetric synthesis of both enantiomers of 4‑substituted 1,4-dihydropyridines with the use of bifunctional thiourea-ammonium salts bearing different counterions

Kohzo Yoshida et al. Molecules. .

Abstract

Organoammonium salts composed of a Brønsted acid and an anilinothiourea promoted the Michael addition of ß-keto esters and α,ß-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 HBF(4) with the same bifunctional thiourea, both enantiomers of 4-substituted 1,4-dihydropyridine were synthesized from the same starting materials.

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Figures

Figure 1
Figure 1
Proposed dual activation mode of aminothiourea.
Scheme 1
Scheme 1
Synthetic routes to 1,4-DHPs.
Figure 2
Figure 2
Structures of thiourea catalysts employed.
Scheme 2
Scheme 2
Synthesis of thiourea (R, R)-1d and 1e.
Scheme 3
Scheme 3
Synthesis of thiourea (R, R)-1f-h.
Figure 3
Figure 3
Proposed TS models for the co-catalyzed three-component reaction.
See this image and copyright information in PMC

References

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