Proline‐Mediated Enantioselective Construction of Tetrahydropyridines <i>via</i> a Cascade Mannich‐Type/Intramolecular Cyclization Reaction

Han, Rong-Gang; Wang, Yao; Li, Yuye; Xu, Peng‐Fei

doi:10.1002/adsc.200800253

Cited by 64 publications

(15 citation statements)

References 50 publications

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“…In 2008, Xu and coworkers [26] reported an enantioselective synthetic method for substituted tetrahydropyridines via a proline-mediated cascade Mannichtype/intramolecular cyclization (Scheme 16). A noteworthy advantage of the method was the NPMP aldimines from inexpensive aqueous materials tetrahydro-2H-pyran-2,6-diol were easily prepared with excellent diastereo-and enantioselectivity in the presence of water.…”

Section: L-proline and Its Derivativesmentioning

confidence: 99%

Recent progress in the asymmetric Mannich reaction

2012

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KEYWORDSThe asymmetric Mannich reaction is one of the most useful carbon-carbon bond forming reactions for the synthesis of chiral molecules containing nitrogen. The resulting β-amino carbonyl compounds are valuable synthons in the preparation of many natural products with useful biological properties. In recent years, asymmetric Mannich processes have increasingly been reported and used in a rapidly growing number of applications. This review provides an overview of the recent history of the applications of various catalytic systems in asymmetric Mannich reaction, including metal-based asymmetric organocatalysis, asymmetric organocatalysis, other chiral catalysis and no chiral catalysis systems. Chiral amine catalysis Chiral Bronsted acid Asymmetric organocatalysis Metal-based organocatalysis Asymmetric Mannich reaction Diastereo-and enantioselective

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Section: L-proline and Its Derivativesmentioning

confidence: 99%

Recent progress in the asymmetric Mannich reaction

2012

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“…Xu and co‐workers reported a diastereo‐ and enantio‐selective synthetic protocol by the application of glutaraldehyde ( 24 ) to produce N ‐heterocycles such as tetrahydropyridines by using primary amine catalysis. A Mannich‐type reaction was developed, which gave 25 in an intramolecular aqueous cyclization of glutaraldehyde, N ‐PMP aldimine 26 and proline ( 27 ) providing the corresponding tetrahydropyridine derivative 28 (Scheme ) …”

Section: Synthesis Of Saturated N‐heterocycles From Dialdehyde Compoundsmentioning

confidence: 99%

“…A Mannich-type reaction was developed, which gave 25 in an intramolecular aqueous cyclization of glutaraldehyde, N-PMP aldimine 26 and proline (27) providing the corresponding tetrahydropyridine derivative 28 (Scheme 3). [46] Kumar et al reported an extension of the above-described procedure. Cycloaddition of glutaraldehyde (24) furnished asymmetric 2,3-disubstituted piperidine framework (29) with reduction in the last step (Scheme 4).…”

Section: Transformation Of Linear Dialdehydes Into N-heterocyclesmentioning

confidence: 99%

Stereocontrolled Synthesis of Functionalized Azaheterocycles from Carbocycles through Oxidative Ring Opening/Reductive Ring Closing Protocols

Kiss

Ouchakour

Ábrahámi

et al. 2019

The Chemical Record

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Fluorine‐containing organic scaffolds are of significant interest in medicinal chemistry. The incorporation of fluorine into biomolecules can lead to remarkable changes in their physical, chemical, and biological properties. There are already many drugs on the market, which contain at least one fluorine atom. Saturated functionalized azaheterocycles as bioactive substances have gained increasing attention in pharmaceutical chemistry. Due to the high biorelevance of organofluorine molecules and the importance of N‐heterocyclic compounds, selective stereocontrolled procedures to the access of new fluorine‐containing saturated N‐heterocycles are considered to be a hot research topic. This account summarizes the synthesis of functionalized and fluorine‐containing saturated azaheterocycles starting from functionalized cycloalkenes and based on oxidative ring cleavage of diol intermediates followed by ring expansion with reductive amination.

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“…1, Scheme 13). 37 This rapid approach involved aldimines 21 derived from aromatic/heteroaromatics/alkenyl aldehydes through proline 2 mediated direct Mannich reaction with glutaraldehyde 37 followed by intramolecular cyclization as one-pot 20 transformation. Recently, Kumar and co-workers documented another interesting application of glutaraldehyde 37 for the asymmetric synthesis of 2,3-substituted piperidines 67 through the [4+2] annulation strategy (eqn.…”

Section: Glutaraldehydementioning

confidence: 99%

Linear dialdehydes as promising substrates for aminocatalyzed transformations

et al. 2015

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Organocatalytic domino reactions involving amine activation of carbonyl compounds have become the latest chemical technology towards the design and development of useful synthetic methods. In this direction, linear dialdehydes such as succinaldehyde, glutaraldehyde, and other homologous compounds have attracted considerable attention as suitable substrates for amine catalyzed transformations. Due to their unique structural features, dialdehydes can easily engage in recreation of cascade/tandem transformations for the synthesis of valuable natural products and drug molecules. In this review article we discuss the current scenario and potential applications of linear dialdehydes as adequate synthetic substrates for amine catalyzed transformations to access biologically important complex scaffolds.

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Proline‐Mediated Enantioselective Construction of Tetrahydropyridines via a Cascade Mannich‐Type/Intramolecular Cyclization Reaction

Abstract: A highly diastereo-and enantioselective synthesis of 2,3-disubstituted tetrahydropyridines was accomplished via a proline-mediated cascade Mannich-type/intramolecular cyclization reaction from preformed N-PMP (p-methoxyphenyl) aldimines and inexpensive aqueous tetrahydro-2H-pyran-2,6-diol.

Cited by 64 publications

References 50 publications

Recent progress in the asymmetric Mannich reaction

Recent progress in the asymmetric Mannich reaction

Stereocontrolled Synthesis of Functionalized Azaheterocycles from Carbocycles through Oxidative Ring Opening/Reductive Ring Closing Protocols

Linear dialdehydes as promising substrates for aminocatalyzed transformations

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