Asymmetric Catalytic Aza‐Diels–Alder/Ring‐Closing Cascade Reaction Forming Bicyclic Azaheterocycles by Trienamine Catalysis

Li, Yang; Barløse, Casper L.; Jørgensen, Julie; Carlsen, Bjørn Dreiø; Jørgensen, Karl Anker

doi:10.1002/chem.201605562

Cited by 2 publications

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“…Acylhydrazones 62,a cting as dienophiles,u nderwent cycloaddition reactions with the trienamines generated in situ from the reactiono ft he 2,4-dienals 61 and the organocatalyst (S)-45.T he intermediate cycloadducts then cyclized via ah emiaminal formation reaction to yield 63 (Scheme 17). [48] Kim and co-workers reported the synthesiso fs ubstitutedd ihydro-( 69 [49] and 71 [50] )o rt etrahydroquinoline derivatives (65, [51] 66, [51] and 68 [49] )w ith excellent stereoselectivities using asymmetric domino reactions catalyzed by the chiral secondary amine catalyst (S)-45.T he reactiono ft he a,b-unsaturated substrates 64 with malonates 67,a ldehydes 70,o ra lkynyl aldehydes 72 led to the formation of compounds 65, 68,a nd 71, respectively.A fter treating compounds 65 and 68 with appropriate reagents,p roducts 66 and 69 were obtained in high yields and ee values,r espectively (Scheme 18).…”

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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“…60 No. 12 activation of a C-H bond in methane during the conversion of natural gas into liquid fuels [181][182][183][184][185][186], the direct synthesis of dimethylcarbonate from methanol [187][188][189][190], and the hydrochlorination of acetylene [191][192][193].…”

Section: Science China Materialsmentioning

confidence: 99%

Graphitized nanocarbon-supported metal catalysts: synthesis, properties, and applications in heterogeneous catalysis

Huang

2017

Sci. China Mater.

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Graphitized nanocarbon materials can be an ideal catalyst support for heterogeneous catalytic systems. Their unique physical and chemical properties, such as large surface area, high adsorption capacity, excellent thermal and mechanical stability, outstanding electronic properties, and tunable porosity, allow the anchoring and dispersion of the active metals. Therefore, currently they are used as the key support material in many catalytic processes. This review summarizes recent relevant applications in supported catalysts that use graphitized nanocarbon as supports for catalytic oxidation, hydrogenation, dehydrogenation, and C-C coupling reactions in liquid-phase and gas-solid phase-reaction systems. The latest developments in specific features derived from the morphology and characteristics of graphitized nanocarbon-supported metal catalysts are highlighted, as well as the differences in the catalytic behavior of graphitized nanocarbon-supported metal catalysts versus other related catalysts. The scientific challenges and opportunities in this field are also discussed. Keywords: nanocarbon materials; graphitized carbon supports; metal catalysts; hetergeneous catalysis INTRODUCTIONCarbon combines its atoms in diverse hybridization states (sp, sp 2 , sp 3 ) to form a variety of polymorphs. These are composed entirely of carbon but have different physical structures and different names, including diamond, graphite, fullerenes, and carbines, among others [1][2][3][4][5]. Because these various and versatile allotropes produce materials with a large range of properties, carbon materials can be used in a number of technological processes, including high-tech catalytic ones [6][7][8][9][10].In heterogeneous catalysis, carbon material plays wellestablished and important roles in a wide range of applications, both as catalyst in its own right and as a unique support material [11][12][13][14][15]. The chemical stability of carbon supports in some specifically aqueous phase biomass conversion surpasses that of metal oxide materials; in addition, carbon materials present other common and key advantages as support materials for catalysis [1,5]. From the point of physical structure, porous carbon can be prepared in different forms (granules, cloth, fibers, pallets, etc.). Due to its chemical properties, carbon structure is resistant to both acidic and basic media. The structure of carbon is stable at high temperature (even above 1023 K under inert atmosphere). The hydrophilic/ hydrophobic nature of carbon can be easily modified. Active metals on the support can be easily reduced. For the purposes of industrial economy and environment, the active phase can be easily recovered. Conventional carbon supports are lower-cost and more easily available than other conventional supports. Although several kinds of carbon materials have been studied, active carbon (AC) [12,[16][17][18][19] and, to a lesser extend, carbon black [20][21][22][23] have long been the most commonly used carbon supports. AC is an amorphous solid prepa...

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Asymmetric Catalytic Aza‐Diels–Alder/Ring‐Closing Cascade Reaction Forming Bicyclic Azaheterocycles by Trienamine Catalysis

Abstract: What is the most significant result of this study?This study presents an ew example of trienamine-catalyzed aza-Diels-Alder reaction providing an ew strategy for the construction of bicyclic aza-heterocycles in an enantioselective manner.

Cited by 2 publications

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Recent Progress in Organocatalytic Asymmetric Domino Transformations

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Graphitized nanocarbon-supported metal catalysts: synthesis, properties, and applications in heterogeneous catalysis

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