Stereoselective One-Pot, Three-Component Synthesis of 4-Amidotetrahydropyran

Reddy, U. C.; Raju, B. Rama; Kumar, E. K. Pramod; Saikia, Anil K.

doi:10.1021/jo7023366

Cited by 40 publications

(12 citation statements)

References 41 publications

(16 reference statements)

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“…Initial investigations were based on tandem Prins–Ritter reaction conditions first reported by Willis and co‐workers for the synthesis of 4‐amidotetrahydropyrans . Yadav and co‐workers have used similar conditions for the formation of 4‐amidopiperidine derivatives, and a Sakurai–Prins–Ritter reaction to prepare 2,6‐disubstituted tetrahydropyrans has also been developed . Thus 1 was treated with benzaldehyde and trifluoromethanesulfonic (triflic) acid in acetonitrile at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds

et al. 2019

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Cyclobutene alcohols undergo Prins cyclisations to generate single diastereomers of novel tricyclic heterocycles with five contiguous stereocentres. The reaction times are significantly shorter (ca. 15 min) than with traditional alkene substrates. Stereoselective aza‐Prins cyclisations of cyclobutene amine derivatives give fused aza‐heterocyclic scaffolds. Computational studies provide insight into the observed stereocontrol. The modular approach is flexible, enabling the introduction of a variety of functional groups (including amides, nitriles, alkynes, and arenes) into the sp3‐rich heterocyclic scaffolds.

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Section: Methodsmentioning

confidence: 99%

Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds

et al. 2019

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“…[14] Yadav et al have used similar conditions for the formation of 4-amidopiperidine derivatives [15] and a Sakurai−Prins−Ritter reaction to prepare 2,6-disubstituted tetrahydropyrans has also been developed. [16][17][18] Thus, 1 was treated with benzaldehyde and triflic acid (TfOH) in acetonitrile at room temperature. After 30 minutes, the starting material had been completely consumed.…”

Section: Scheme 1 Proposed Synthesis Of Tricyclic Heterocyclesmentioning

confidence: 99%

Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds

et al. 2019

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Cyclobutene alcohols undergo Prins cyclizations to generate single diastereomers of novel tricyclic heterocycles with five contiguous stereocenters. Reaction times are significantly shorter (~15 mins) than with traditional alkene substrates. Stereoselective aza-Prins cyclizations of cyclobutene amine derivatives give fused aza-heterocyclic scaffolds. Computational studies provide insight into the observed stereocontrol. The modular approach is flexible enabling the introduction of a variety of functionality (including amides, nitriles, alkynes and arenes) to the sp 3-rich heterocyclic scaffolds with scope.

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“…A one‐pot Sakurai/Prins/Ritter sequence was explored by Rovis and others . In Rovis' approach acid‐catalyzed reactions between 4‐acetoxy‐1,3‐dioxanes and allylsilanes occur by initial ionization of the more reactive acetal to give an oxocarbenium ion, which readily undergoes Sakurai allylation.…”

Section: Synthesis Of Oxacycles By Silyl‐prins Cyclizationmentioning

confidence: 99%

Synthesis of O‐ and N‐Heterocycles by Silyl‐Prins Cyclization of Allylsilanes

Díez-Poza

Barbero

2017

Eur J Org Chem

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Prins cyclization has emerged as one of the most valuable methods for the construction of heterocycles. It proceeds through intramolecular addition of a π‐nucleophile to an oxocarbenium or related ion. The use of electron‐rich alkenes, such as allylsilanes (so‐called silyl‐Prins cyclization) offers the benefit of allowing more selective reactions. The regio‐ and stereochemical outcomes of these transformations are explained by well‐stablished transition states. This review presents the most important contributions involving silyl‐Prins cyclization to the stereoselective preparation of oxygen and nitrogen heterocycles. The influence of different structural variants in the selectivity of the cyclization is discussed. These reactions have frequently been used as key steps in the synthesis of a wide variety of natural products.

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Stereoselective One-Pot, Three-Component Synthesis of 4-Amidotetrahydropyran

Abstract: The reaction of aldehyde with allylsilane in acetonitrile mediated by boron trifluoride etherate generated 4-aminotetrahydropyrans in good yields. The product is highly stereoselective.

Cited by 40 publications

References 41 publications

Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds

Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds

Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds

Synthesis of O‐ and N‐Heterocycles by Silyl‐Prins Cyclization of Allylsilanes

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