Tandem Prins/Wagner/Ritter process for the stereoselective synthesis of (3-oxabicyclo[4.2.0]octanyl)amide and (1-(5-aryltetrahydrofuran-3-yl)cyclobutyl)amide derivatives

Reddy, B. V. Subba; Muralikrishna, Katta; Yadav, J. S.; Babu, Neelaiah; Sirisha, K.; Sarma, Akella V. S.

doi:10.1039/c5ob00031a

Cited by 9 publications

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“…In general, the Prins‐Ritter reaction has been reported with acetonitrile (both as a nucleophile and as a solvent) or in CH 2 Cl 2 , in the case of other nitriles . The commonly used catalysts for this transformation are Lewis (Bi(OTf) 3 , BF 3 ⋅Et 2 O, I 2 /AcCl etc.)…”

Section: Introductionmentioning

confidence: 99%

Stereoselectivity Inversion by Water Addition in the −SO₃H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives

et al. 2020

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A range of heterogeneous -SO 3 H functionalized catalysts including carbon and halloysite nanotubes, commercial K10 clay, Amberlyst-15 etc. was investigated for the first time using as a model the Prins-Ritter reaction of (À )-isopulegol with benzaldehyde and acetonitrile producing 4-amido derivatives of octahydro-2H-chromenes (as (S)-and (R)-diastereomers). A strong effect of water addition prior the reaction on the overall selectivity and the ratio of isomers in the case of heterogeneous and homogeneous (p-toluenesulfonic acid) catalysis was found for the first time. The yield of the (R)-diastereomer sharply increased with increasing amount of added water, while the S-isomer prevailed with a minimum amount of added water. Experimental results and DFT calculations clearly indicate a kinetic control for R-amide formation. Typically synthesis of 4amidooctahydro-2H-chromenes requires subzero temperatures and toxic catalysts, which were avoided in the current work. Nevertheless, the yield of the desired products (up to 83 %) at 30°C after water addition exceeded the values reported previously. Thus, adding water is a simple and a very effective method for controlling both the yield and stereoselectivity of the Prins-Ritter reaction products under mild conditions.

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Section: Introductionmentioning

confidence: 99%

Stereoselectivity Inversion by Water Addition in the −SO₃H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives

et al. 2020

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ChemInform Abstract: Tandem Prins/Wagner/Ritter Process for the Stereoselective Synthesis of (3‐Oxabicyclo[4.2.0]octanyl)amide and (1‐(5‐Aryltetrahydrofuran‐3‐yl)cyclobutyl)amide Derivatives.

et al. 2015

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Tandem Prins/Wagner/Ritter Process for the Stereoselective Synthesis of (3-Oxabicyclo[4.2.0]octanyl)amide and (1-(5-Aryltetrahydrofuran-3-yl)cyclobutyl)amide Derivatives. -Three-component reaction of vinylcyclopropyl carbinol (I), aldehydes, and nitriles provides access to the novel oxabicyclooctanyl amides [cf. (IV), (VII)], whilst (1-vinylcyclobutyl)methanol (VII) gives cyclobutyltetrahydrofuran derivatives (IX) under similar conditions. Surprisingly, three-component reaction of carbinol (I) with MeCN and cinnamaldehyde furnishes alcohol (XI) instead of an expected amide. -(SUBBA REDDY*, B. V.; MURALIKRISHNA, K.; YADAV, J. S.; BABU, N. J.; SIRISHA, K.; SARMA, A. V. S.; Org. Biomol. Chem. 13 (2015) 19, 5532-5536, http://dx.doi.org/10.1039/C5OB00031A ; Nat. Prod. Chem., Indian Inst. Chem. Technol., Hyderabad 500 007, India; Eng.) -H. Toeppel 37-162

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Access to Polyfluorinated Tetrahydropyranyl Amides via Prins‐Ritter Cyclization under Green Conditions

et al. 2019

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Tandem Prins/Wagner/Ritter process for the stereoselective synthesis of (3-oxabicyclo[4.2.0]octanyl)amide and (1-(5-aryltetrahydrofuran-3-yl)cyclobutyl)amide derivatives

Cited by 9 publications

References 20 publications

Stereoselectivity Inversion by Water Addition in the −SO₃H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives

Stereoselectivity Inversion by Water Addition in the −SO₃H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives

ChemInform Abstract: Tandem Prins/Wagner/Ritter Process for the Stereoselective Synthesis of (3‐Oxabicyclo[4.2.0]octanyl)amide and (1‐(5‐Aryltetrahydrofuran‐3‐yl)cyclobutyl)amide Derivatives.

Access to Polyfluorinated Tetrahydropyranyl Amides via Prins‐Ritter Cyclization under Green Conditions

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Tandem Prins/Wagner/Ritter process for the stereoselective synthesis of (3-oxabicyclo[4.2.0]octanyl)amide and (1-(5-aryltetrahydrofuran-3-yl)cyclobutyl)amide derivatives

Cited by 9 publications

References 20 publications

Stereoselectivity Inversion by Water Addition in the −SO3H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives

Stereoselectivity Inversion by Water Addition in the −SO3H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives

ChemInform Abstract: Tandem Prins/Wagner/Ritter Process for the Stereoselective Synthesis of (3‐Oxabicyclo[4.2.0]octanyl)amide and (1‐(5‐Aryltetrahydrofuran‐3‐yl)cyclobutyl)amide Derivatives.

Access to Polyfluorinated Tetrahydropyranyl Amides via Prins‐Ritter Cyclization under Green Conditions

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Stereoselectivity Inversion by Water Addition in the −SO₃H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives

Stereoselectivity Inversion by Water Addition in the −SO₃H‐catalyzed Tandem Prins‐Ritter Reaction for Synthesis of 4‐amidotetrahydropyran Derivatives