Enantioselective synthesis of proline derivatives by 1,3-dipolar cycloadditions

Nájera, Carmén; Sansano, José M.

doi:10.1007/s00706-011-0467-9

Cited by 18 publications

(2 citation statements)

References 110 publications

(45 reference statements)

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“…The contribution in this field concerns the elaboration of the GSK's first and second generation polymerase inhibitors through enantioselective processes based on silver(I)-and gold(I)-catalyzed 1,3-dipolar cycloadditions of azomethine ylides. 75,76 Scheme 29. Synthesis of pyridine/pyridinium-type fullerene derivatives.…”

Section: Synthesis Of Antiviral Compounds Through Azomethine Ylidesmentioning

confidence: 99%

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions. Part 2: nitrones, nitrile oxides and imines, and other 1,3-dipoles

Quadrelli¹,

Mella²,

Faita³

2023

Arkivoc

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Prominent in the current stage of drug development, antiviral compounds can be efficiently prepared through cycloaddition reactions. This review reports the use of 1,3-dipolar cycloadditions of nitrones, nitrile oxides and imines and other 1,3-dipoles in the light of their application for the preparation of synthons in the design and synthesis of compounds that were tested for their antiviral activities against a variety of viruses. Since nitrile oxides represent valuable precursors of nitrosocarbonyl intermediates, their use in the synthesis of antiviral compounds is reported. The products obtained from these pericyclic reaction approaches were tested for their activities in terms of blocking the virus replication and the relevant biological data are highlighted.

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Section: Synthesis Of Antiviral Compounds Through Azomethine Ylidesmentioning

confidence: 99%

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions. Part 2: nitrones, nitrile oxides and imines, and other 1,3-dipoles

Quadrelli¹,

Mella²,

Faita³

2023

Arkivoc

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“…The dipolar cycloaddition reaction is a known and widely studied method in organic synthesis to obtain pyrrolidine derivatives from the reaction of azomethine ylides, generated in situ , and electron-deficient olefins [7,8,9]. These five-membered ring systems belong to an important class of aza-compounds with multiple applications, for example, in the development of bioactive molecules, organocatalysts, new materials and as scaffolds in total organic synthesis [10,11,12,13].…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient and Diastereoselective Synthesis of New Pyrazolylpyrrolizine and Pyrazolylpyrrolidine Derivates by a Three-Component Domino Process

et al. 2014

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Asymmetric Synthesis of Hexahydropyrrolo‐isoquinolines by an Organocatalytic Three‐Component Reaction

Fraile

Schietroma

Albrecht

et al. 2012

Chemistry A European J

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The pyrrolo-isoquinoline moiety [1] is present in alkaloid families such as erythrines, [2] lamellarins, [3] and pyrroloA C H T U N G T R E N N U N G [2,1-a]isoquinoline derivatives, [4, 5] all of which exhibit biological activities. The importance of this heterocyclic system is further enhanced by its utility as an intermediate for the synthesis of alkaloids.[1] Consequently, the interest in new synthetic methodologies for this moiety has increased.[6] Three strategies have been developed for the asymmetric construction of polyhydropyrroloA C H T U N G T R E N N U N G [2,1-a]isoquinoline derivatives: a) N-acyliminium cyclization, [7] b) Mitsunobu reaction of optically pure 3-(tetrahydroisoquinolin-1-yl)propan-1-oles, [4a, 8] and c) asymmetric hydrogenation of prochiral iminium salts with a chiral metal complex. [4b, 9] A diastereoselective route to this moiety involving a [3+2]-cycloaddition of 3,4-dihydroisoquinolinium ylides to chiral dipolarophiles was recently presented. [10] One strategy to optically active polysubstituted pyrrolidines is the metal- [11] or organocatalyzed [11c, 12] [3+2]-cycloaddition of alkenes with azomethines. However, these reactions focus on a-iminoesters as azomethine ylide precursors and only recently has an organocatalytic [3+2]-cycloaddition of azomethine ylides to a,b-unsaturated aldehydes been presented.[13]Herein we present a new multicomponent [14] concept for the construction of hexahydropyrroloA C H T U N G T R E N N U N G [2,1-a]isoquinoline derivatives. The concept is based on a [3+2]-cycloaddition reaction of in situ generated dihydroisoquinolinium ylides, from the corresponding imines and a-bromoesters or ketone, [15] to a,b-unsaturated aldehydes, and is catalyzed by a chiral pyrrolidine in the presence of a base (Scheme 1). This multicomponent approach allows the formation of two new CÀC bonds, a CÀN bond, and four stereocenters in one-step.The three-component reaction between 6,7-dimethoxy-3,4-dihydroisoquinoline HCl (1 a), methyl 2-bromopropanoate (2 a), and cinnamic aldehyde (3 a) was the model system for optimization of the experimental parameters. [16] (S)-2-(Diphenyl(trimethylsilyloxy)methyl)pyrrolidine (4 a),[17] Na 2 CO 3 , CH 2 Cl 2 , and room temperature were the best conditions for the [3+2]-cycloaddition and gave the optically active product, as the conjugated ester 5 a, in high yields, good diastereoselectivity and an excellent enantioselectivity of 95 % ee.The scope of the three-component [3+2]-cycloaddition using different a,b-unsaturated aldehydes is given in Table 1.

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Enantioselective synthesis of proline derivatives by 1,3-dipolar cycloadditions

Cited by 18 publications

References 110 publications

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions. Part 2: nitrones, nitrile oxides and imines, and other 1,3-dipoles

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions. Part 2: nitrones, nitrile oxides and imines, and other 1,3-dipoles

Highly Efficient and Diastereoselective Synthesis of New Pyrazolylpyrrolizine and Pyrazolylpyrrolidine Derivates by a Three-Component Domino Process

Asymmetric Synthesis of Hexahydropyrrolo‐isoquinolines by an Organocatalytic Three‐Component Reaction

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