Stereoselective synthesis of 5-(1-aminoalkyl)-2-pyrrolidones and 1,7-diazaspiro[4.5]decane-2,8-diones from chiral N-tert-butanesulfinyl imines and ethyl 4-nitrobutanoate

Hernández-Ibáñez, Sandra; Barros, Olga Soares do Rego; Lahosa, Alejandro; García-Muñoz, M. Jesús; Benlahrech, Meriem; Behloul, Cherif; Foubelo, Francisco; Yus, Miguel

doi:10.1016/j.tet.2019.130842

Cited by 4 publications

(3 citation statements)

References 78 publications

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“…Further transformation of the nitro group under Nef-type reaction conditions led to enantioenriched 6-substituted piperidine-2,5-diones 206 [142]. Interestingly, from compounds 205, and following a two-step process, involving conjugative addition to ethyl acrylate with formation of 207 as a single diastereoisomer, and final reduction of the nitro group with Raney-nickel, 1,7diazaspiro [4.5]decane-2,8-diones 208 were accessed in a highly stereoselective fashion (Scheme 50) [143].…”

Section: Cyclizations Involving a Position In The Attacking Nucleophilementioning

confidence: 99%

“…Heterocyclic compounds can be obtained through strategies using Mannich reactions [164][165][166]. It was previously commented that the addition of ethyl 4-nitrobutanoante (203) to chiral sulfinyl imines under basic solvent-free conditions proceeded with high facial diastereoselectivity (Scheme 64 [143]). When the reaction was performed with the imine of 5-bromopentanal, (R S )-76, the nitro-Mannich adduct 292 was formed in 86% yield as a 1:1 mixture of diastereoisomers, considering the stereocenter bearing the nitro group.…”

Section: Stereocontrol Synthesis Through Mannich Nitro-mannich and Mukaiyama-mannich Reactions Of N-sulfinyl Iminesmentioning

confidence: 99%

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N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

Mendes¹,

Costa²,

Yus³

et al. 2021

Beilstein J. Org. Chem.

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The synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from tert-butanesulfinamide. These imines are versatile chiral auxiliaries and have been extensively used as eletrophiles in a wide range of reactions. The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the tert-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles. The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral N-tert-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products. The synthesis of nitrogen-containing heterocycles in which the nitrogen atom is not provided by the chiral imine will not be considered in this review. The sections are organized according to the size of the heterocycles. The present work will comprehensively cover the most pertinent contributions to this research area from 2012 to 2020. We regret in advance that some contributions are excluded in order to maintain a concise format.

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Section: Cyclizations Involving a Position In The Attacking Nucleophilementioning

confidence: 99%

Section: Stereocontrol Synthesis Through Mannich Nitro-mannich and Mukaiyama-mannich Reactions Of N-sulfinyl Iminesmentioning

confidence: 99%

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

Mendes¹,

Costa²,

Yus³

et al. 2021

Beilstein J. Org. Chem.

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“…This has significantly facilitated the use of these imines for obtaining the corresponding enantioenriched primary amines. These amine derivatives have proven valuable in the synthesis of enantioenriched N - heterocycles, natural alkaloids, and other biologically active compounds …”

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confidence: 99%

Stereoselective Synthesis of Densely Substituted Pyrrolidines via a [3 + 2] Cycloaddition Reaction between Chiral N-tert-Butanesulfinylazadienes and Azomethine Ylides

Blanco-López,

Foubelo,

Retamosa

et al. 2023

Org. Lett.

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The N-tert-butanesulfinylimine group behaves as a suitable electron-withdrawing group in 1-azadienes, allowing the diastereoselective synthesis of densely substituted pyrrolidines by 1,3-dipolar cycloadditions (1,3-DCs) with azomethylene ylides. The use of Ag2CO3 as catalyst has allowed one to obtain a wide variety of proline derivatives with high regio- and diastereoselectivities. Subsequent efficient transformations provide valuable proline derivatives, some of which can be used as organocatalysts. The influence of the N-tert-butanesulfinyl group on the diastereoselectivity was studied by computational methods.

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Transition metal-catalyzed reactions of N-sulfinyl imines

Foubelo

Nájera

Sansano

et al. 2021

Tetrahedron Letters

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Stereoselective synthesis of 5-(1-aminoalkyl)-2-pyrrolidones and 1,7-diazaspiro[4.5]decane-2,8-diones from chiral N-tert-butanesulfinyl imines and ethyl 4-nitrobutanoate

Cited by 4 publications

References 78 publications

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

Stereoselective Synthesis of Densely Substituted Pyrrolidines via a [3 + 2] Cycloaddition Reaction between Chiral N-tert-Butanesulfinylazadienes and Azomethine Ylides

Transition metal-catalyzed reactions of N-sulfinyl imines

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