Chiral Phase Transfer Catalysts for the Synthesis of Chiral <i>N</i>‐Heterocycles <i>via</i>Asymmetric Cascade Reactions

Tiso, Silvia; Massa, António

doi:10.1002/jhet.2170

Cited by 13 publications

(14 citation statements)

References 57 publications

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“…[169] They also demonstrated that this strategy may be further extended to produce ent-436 and ent-437 by using 440 (Scheme 112) as ac hiral phase-transfer catalyst. [170] Enders and co-workers reported as tereoselective synthesiso fe nantioenriched tetrahydropyridines 442 with high yields and excellent stereoselectivities from the intermediates 441,which were formed via Michael addition reactions between nitroalkenes 76 and1 ,3-diketones 379,c atalyzed by aq uinine-derived squaramide 443 (Scheme 113). [171] Thei ntermediates 441 underwent ad omino aza-Henry/cyclization reaction with the pre-formed aldimines 444 to afford the final products 442.T he reactionm ay also be carried out by adding all three of the substratest ogether at the beginningoft he reaction.…”

Section: 211synthesis Of Aza-heterocyclesmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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Sustainability in chemical synthesis is a major aspect of the current synthetic endeavors and, therefore,m imicking the biological process in the laboratory nowadays has the highest priority.T owards achieving this goal, designingorganic reactions in domino mode rathert han the multistep synthetic pathways andu sing organocatalysisi nstead of metal catalysis have received al ot of attention due to the inherenta dvantageso ft hese processes in terms of synthetic efficiencya nd sustainability.A saresult, the field of asymmetric organocatalytic domino reactions has witnessed tremendous progress in recent years.T his review attempts to summarize the latest developments in asymmetric organocatalyzed domino reactions since 2012, with the emphasis on the catalysts andr eactionm odes.D iscussions on the reactionm echanismsa nd the applications of the developed domino reactionm ethodsi nt he synthesis of biologically active molecules and natural products are also includedwhen appropriate.

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Section: 211synthesis Of Aza-heterocyclesmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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“…However,t he preparation of the aforementioned starting materials 73 required al ong synthetic pathway.C ascade reactions were naturally taken into account to overcome this shortcoming. In 2015, [39] Massa and co-workersr eporteda ne fficient cascade reactiono f2 -cyanobenzaldehyde 75 with active methylene compounds 76,r esulting in chiral products 77,w hich furtherr eacted with acrylaldehyde to form fused products 78 (Scheme 18). Various catalysts have been investigated and PTC-3,b earing an urea-quinine bifunctional group, was an appropriate choice.…”

Section: Phase Transfer Catalyzed Asymmetric Synthesis Of Isoindolinonesmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Isoindolinones

Gao

Chen

Ding

et al. 2019

Chemistry An Asian Journal

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As important reactive species, isoindolinones represent a cluster of valuable building blocks for the construction of natural‐product‐like compounds. In particular, chiral isoindolinones are the key structural feature of naturally occurring bioactive molecules. During the past decade, great advances have been made in the asymmetric synthesis of isoindolinone skeleton compounds. Hence, recent progress in catalytic asymmetric synthesis of isoindolinones is reviewed here, with emphasis on chiral organocatalysis and transition metal complexes enabled transformations. Different organocatalysts (chiral phosphoric acids, phase transfer catalysts, chiral thioureas) and chiral transition‐metal complexes (Rh, Pd, Ir, Cu, Mg, and Ni) are included in this transformation.

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“…Normally, three‐component reactions of 112 a , amine, and a nucleophile produce isoindolinones, but similar reactions with 2‐cyanobenzaldehyde tended to give isoindolin‐1‐imine derivatives in some cases . 2‐Substituted 3‐alkoxyisoindolin‐1‐imine derivatives could be obtained through the three‐component condensation of 2‐cyanobenzaldehyde, amine, and alcohol . Synthetic reactions of 3‐substituted isoindolinones from 2‐cyanobenzaldehyde have also been derivatized into an asymmetrical version with the aid of a phase‐transfer catalyst derived from bifunctional urea–quinine …”

Section: Benzaldo‐x Bifunctional Building Blocks and Their Heterocyclmentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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Chiral Phase Transfer Catalysts for the Synthesis of Chiral N‐Heterocycles viaAsymmetric Cascade Reactions

Cited by 13 publications

References 57 publications

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Catalytic Asymmetric Synthesis of Isoindolinones

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

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