Regio and diastereoselective multicomponent 1,3-dipolar cycloadditions between prolinate hydrochlorides, aldehydes and dipolarophiles for the direct synthesis of pyrrolizidines

Mancebo‐Aracil, Juan; Nájera, Carmén; Castelló, Luis M.; Sansano, José M.; Larrañaga, Olatz; Cózar, Abel de; Cossío, Fernando P.

doi:10.1016/j.tet.2015.10.064

Cited by 16 publications

(12 citation statements)

References 76 publications

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“…We next transferred our attention to evaluate the three-component one-pot 1,3-dipolar cycloaddition of the in situ generated α-iminoesters from tert-butyl glycinate and different aromatic aldehydes under the action of N,N'-Diisopropylcarbodiimide (DIC) serving as a dehydrator with α-methylene-γ-butyrolactone 3 [29,30]. As shown in Scheme 3, arene-substituents with different electronic properties and steric hindrance were well tolerated and the desired endo-6a-6f were obtained in one-pot process with excellent yields (92%-97%) and moderate to high enantioselectivities (66%-90% ee).…”

Section: Study On the Construction Of Spiro Pyrrolidines By The Threementioning

confidence: 99%

Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone

et al. 2019

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Construction of spirocyclic pyrrolidines bearing a spiro quaternary stereocenter is an enormous challenge in synthetic organic chemistry. In this report, we introduce a Ag(I)/CAAA-amidphos-catalyzed enantioselective 1,3-dipolar cycloaddition between azomethine ylides and α-methylene-γ-butyrolactone as an effective strategy for the construction of excellent endo-selective spiro-[butyrolactone-pyrrolidine] derivatives. Meanwhile, the catalytic system was also successfully applied in the three-component one-pot reaction of azomethine ylides formed in situ under the action of N,N′-diisopropylcarbodiimide serving as a dehydrator. Under the optimal conditions, endo-pyrrolidine derivatives bearing a spiro quaternary stereocenter were obtained with high to excellent yields (up to 95% yield) and enantioselectivities (up to 93% ee).

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Section: Study On the Construction Of Spiro Pyrrolidines By The Threementioning

confidence: 99%

Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone

et al. 2019

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“…However, working in the presence, or in the absence of AgOAc, and N-methylmaleimide as dipolarophile, a 3:1 mixture of diastereomeric adducts 77 and 78 were obtained [54] (Fig. 6).…”

Section: Multicomponent Synthesis Of Pyrrolizidines By 13-dcmentioning

confidence: 99%

Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

Nájera

Sansano

2018

Pure and Applied Chemistry

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Different multicomponent 1,3-dipolar cycloadditions (1,3-DC) of cyclic α-amino acid derivatives with aldehydes and dipolarophiles have been described as efficient and simple methodologies for the synthesis of the pyrrolidine unit of pyrrolizidines and indolizidines. When free cyclic α-amino acids are used, a thermal promoted decarboxylative process generates in situ the corresponding non-stabilized azomethine ylides, which afforded the corresponding pyrrolizidines and indolizidines with a hydrogen in the bicyclic units. This methodology has been employed to the synthesis of complex systems including spiro derivatives when ketones are used as carbonyl component. In addition, working with cyclic α-amino acid derived esters, the three-component 1,3-DC takes place under milder reaction conditions giving the corresponding pyrrolizidines and indolizidines with an alkoxycarbonyl group in the bridge adjacent carbon to the nitrogen. This methodology can be carried out by a double consecutive or stepwise 1,3-DC to provide pyrrolizidines via the precursor prolinates. The conformation of the azomethine ylide controls the endo/exo diastereoselectivity of the 1,3-DC.

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“…The reaction proceeded with both high regio-and diastereoselectivity to yield heterocycles in the presence or in the absence of AgOAc as catalyst depending on the aldehyde employed (Scheme 82). 123 This cascade allowed access to diverse molecular complexity, multiplication of stereocenters, and access to potential bioactive pyrrolizidine alkaloids.…”

Section: Scheme 81 Synthesis Of Functionalized Spiropyrrolizidines Anmentioning

confidence: 99%

Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides

2017

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In this revision a summary of the trends of the formation of complex or not so complex heterocyclic structures through 1,3-DC of azomethine ylides is described. Diastereo-and enantioselective processes as well as nonasymmetric cycloadditions constitute very important synthetic tools for achieving all these series of compounds. The contents are classified as follows: 1. Introduction 2. Synthesis of spiroxindoles 3. Synthesis of spiropyrrolidines 4. Synthesis of spiropiperidines and piperidines 5. Synthesis of pyrrolidines and fused pyrrolidines 6. Synthesis of pyrrolizidines and indolizidines 7. Synthesis of quinolone and isoquinolines 8. Conclusions

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Regio and diastereoselective multicomponent 1,3-dipolar cycloadditions between prolinate hydrochlorides, aldehydes and dipolarophiles for the direct synthesis of pyrrolizidines

Cited by 16 publications

References 76 publications

Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone

Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone

Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides

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