H8-BINOL chiral imidodiphosphoric acids catalyzed cyclization reactions of β,γ-unsaturated α-ketoesters, arylamines and 1,3-dicarbonyl compounds: enantioselective synthesis of 1,4-dihydropyridines

An, Dong; Zhu, Zhen; Zhang, Guangliang; Gao, Jigang; Han, Xu; Zheng, Liangyu; Zhang, Suoqin

doi:10.1016/j.tetasy.2015.06.019

Cited by 25 publications

(12 citation statements)

References 43 publications

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“…In 2015, Zhang's group reported an enantioselective cyclization between β,γ-unsaturated α-ketoesters 9, arylamines 5 and acetylacetone 4c, giving rise to penta-substituted 1,4-DHPs 3 with moderate yields (34-61%) and good to excellent selectivity (75-97% ee, Scheme 7). [16] The reaction is catalyzed by the H 8 -BINOL type chiral imidodiphosphoric acid V with better activity than a normal chiral phosphoric acid. [26] Scheme 7.…”

Section: Methodsmentioning

confidence: 99%

“…Figure 2. Enantioselective organocatalytic synthesis of 1,4-DHPs: Catalysts and results [I, [12] II, [13] III, [14] IV, [15] V, [16] VI, [17,18] VII, [19,20] VIII, [21] and IX [22,23] ]…”

Section: Introductionmentioning

confidence: 99%

“…Scheme 2. Synthetic routes for chiral 1,4-DHPs [(a), [13,[18][19][20][21] (b), [12] (c), [16] (d), [15] (e), [17] (f), [14] and (g) [21,23] ].…”

Section: Introductionmentioning

confidence: 99%

“…The first method, developed by Renaud, dates from 2007, and yielded a modest 50% ee, using a phosphoric acid derivative as catalyst (II; route a). [13] Since then, different organocatalysts have been tested for this purpose, such as other phosphoric acid derivatives following multicomponent strategies (I, [12] III [14] and V; [16] routes b, f and c, respectively). Chiral phosphoric acid IV has been also used together with Y(OTf) 3 forming a dual catalytic system (route d).…”

Section: Introductionmentioning

confidence: 99%

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Organocatalytic Enantioselective Synthesis of 1,4‐Dihydropyridines

2017

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This review aims to bring light upon a very interesting group of compounds, the 1,4-dihydropyridines (1,4-DHPs). These structures are well-known pharmacophores, used for many years to treat cardiovascular diseases because of their activity as calcium channel blockers. In addition, their potential as drugs to treat other affections has been recently exposed. The racemic synthesis of 1,4-DHPs has been well studied, while the asymmetric approaches are mainly based on the use of chiral auxiliaries or chiral resolutions. However, there are scarce examples regarding enantioselective organocatalytic methods. Herein, we will summarize the existing examples in this field of research. 1 Introduction 2 BINOL-derived phosphoric acid mediated organocatalysis 3 (Thio)urea mediated organocatalysis 4 Aminocatalysis 5 Dual catalysis 6 Summary and outlook

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Section: Methodsmentioning

confidence: 99%

“…Figure 2. Enantioselective organocatalytic synthesis of 1,4-DHPs: Catalysts and results [I, [12] II, [13] III, [14] IV, [15] V, [16] VI, [17,18] VII, [19,20] VIII, [21] and IX [22,23] ]…”

Section: Introductionmentioning

confidence: 99%

“…Scheme 2. Synthetic routes for chiral 1,4-DHPs [(a), [13,[18][19][20][21] (b), [12] (c), [16] (d), [15] (e), [17] (f), [14] and (g) [21,23] ].…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Organocatalytic Enantioselective Synthesis of 1,4‐Dihydropyridines

2017

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“…Chiral imidodiphosphoric acids have achieved much attention and have been used in variety of ring-closing reactions since 2012. [10][11][12] Scheme1.Asymmetric synthesis of six-and seven-membered rings via Pictet-Spengler-type reaction.…”

mentioning

confidence: 99%