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Open AccessReview

Recent Approaches to Chiral 1,4-Dihydropyridines and their Fused Analogues

1
Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga LV-1006, Latvia
2
Department of Regenerative Medicine, State Research Institute Centre for Innovative Medicine, Santariskiu 5, LT-08406 Vilnius, Lithuania
3
Department of Chemical Engineering, National Taiwan University, 1, Roosevelt Rd. Sec. 4, Taipei 106, Taiwan
*
Author to whom correspondence should be addressed.
Catalysts 2020, 10(9), 1019; https://doi.org/10.3390/catal10091019
Received: 11 August 2020 / Revised: 26 August 2020 / Accepted: 28 August 2020 / Published: 4 September 2020
(This article belongs to the Special Issue Catalysis in Heterocyclic and Organometallic Synthesis)
The purpose of this review is to highlight recent developments in the synthesis of chiral 1,4-dihydropyridines and their fused analogues. 1,4-Dihydropyridines are among the most active calcium antagonists that are used for the treatment of hypertension. Enantiomers of unsymmetrical 1,4-dihydropyridines often show different biological activities and may have even an opposite action profile. Hantzsch synthesis usually produces racemic mixtures of unsymmetrical 1,4-dihydropyridines. Therefore, the development of stereoselective synthesis of 1,4-dihydropyridines is one of the priorities of medicinal chemistry. Over the years, numerous methodologies have been developed for the production of enantiopure 1,4-dihydropyridines, such as stereoselective synthesis using chiral auxiliaries and chiral cyclocondensation partners, chromatographical methods, resolution of diastereomeric 1,4-dihydropyridine salts, enzyme catalysed kinetic resolution, or asymmetrisation of ester groups of 1,4-dihydropyridines. These approaches have been studied in detail and are relatively well established. The catalytic asymmetric approach holds the greatest promise in delivering the most practical and widely applicable methods. Substantial progress has been made toward the development of enantioselective organocatalytic methods for the construction of the chiral dihydropyridines. However, most of them do not provide a convenient way to pharmacologically important 1,4-dihydropyridine-3,5-dicarboxylates. Organocatalytic enantioselective desymmetrisation of prochiral 1,4-dihydropyridine-3,5-dicarbaldehydes also has great promise in the synthesis of pharmacologically important 1,4-dihydropyridine-3,5-dicarboxylates. View Full-Text
Keywords: six-membered N-heterocycles; 1,4-dihydropyridines; calcium channel antagonists; chirality; enzyme-catalysed hydrolysis; resolution of diastereomeric salts; separation; multicomponent reactions; asymmetric synthesis; organocatalysis six-membered N-heterocycles; 1,4-dihydropyridines; calcium channel antagonists; chirality; enzyme-catalysed hydrolysis; resolution of diastereomeric salts; separation; multicomponent reactions; asymmetric synthesis; organocatalysis
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MDPI and ACS Style

Rucins, M.; Plotniece, A.; Bernotiene, E.; Tsai, W.-B.; Sobolev, A. Recent Approaches to Chiral 1,4-Dihydropyridines and their Fused Analogues. Catalysts 2020, 10, 1019. https://doi.org/10.3390/catal10091019

AMA Style

Rucins M, Plotniece A, Bernotiene E, Tsai W-B, Sobolev A. Recent Approaches to Chiral 1,4-Dihydropyridines and their Fused Analogues. Catalysts. 2020; 10(9):1019. https://doi.org/10.3390/catal10091019

Chicago/Turabian Style

Rucins, Martins; Plotniece, Aiva; Bernotiene, Eiva; Tsai, Wei-Bor; Sobolev, Arkadij. 2020. "Recent Approaches to Chiral 1,4-Dihydropyridines and their Fused Analogues" Catalysts 10, no. 9: 1019. https://doi.org/10.3390/catal10091019

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