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

Standard

Stereoselectivity Inversion by Water Addition in the −SO₃H-catalyzed Tandem Prins-Ritter Reaction for Synthesis of 4-amidotetrahydropyran Derivatives. / Sidorenko, Alexander Yu; Li-Zhulanov, Nikolai S.; Mäki-Arvela, Päivi et al.

In: ChemCatChem, Vol. 12, No. 9, 07.05.2020, p. 2605-2609.

Research output: Contribution to journal › Article › peer-review

Harvard

Sidorenko, AY, Li-Zhulanov, NS, Mäki-Arvela, P, Sandberg, T, Kravtsova, AV, Peixoto, AF, Freire, C, Volcho, KP, Salakhutdinov, NF, Agabekov, VE & Murzin, DY 2020, 'Stereoselectivity Inversion by Water Addition in the −SO₃H-catalyzed Tandem Prins-Ritter Reaction for Synthesis of 4-amidotetrahydropyran Derivatives', ChemCatChem, vol. 12, no. 9, pp. 2605-2609. https://doi.org/10.1002/cctc.202000070

APA

Sidorenko, A. Y., Li-Zhulanov, N. S., Mäki-Arvela, P., Sandberg, T., Kravtsova, A. V., Peixoto, A. F., Freire, C., Volcho, K. P., Salakhutdinov, N. F., Agabekov, V. E., & Murzin, D. Y. (2020). Stereoselectivity Inversion by Water Addition in the −SO₃H-catalyzed Tandem Prins-Ritter Reaction for Synthesis of 4-amidotetrahydropyran Derivatives. ChemCatChem, 12(9), 2605-2609. https://doi.org/10.1002/cctc.202000070

Vancouver

Sidorenko AY, Li-Zhulanov NS, Mäki-Arvela P, Sandberg T, Kravtsova AV, Peixoto AF et al. Stereoselectivity Inversion by Water Addition in the −SO₃H-catalyzed Tandem Prins-Ritter Reaction for Synthesis of 4-amidotetrahydropyran Derivatives. ChemCatChem. 2020 May 7;12(9):2605-2609. doi: 10.1002/cctc.202000070

Author

Sidorenko, Alexander Yu ; Li-Zhulanov, Nikolai S. ; Mäki-Arvela, Päivi et al. / Stereoselectivity Inversion by Water Addition in the −SO₃H-catalyzed Tandem Prins-Ritter Reaction for Synthesis of 4-amidotetrahydropyran Derivatives. In: ChemCatChem. 2020 ; Vol. 12, No. 9. pp. 2605-2609.

BibTeX

@article{90d4f98d14634375bc970374fe75cfce,

title = "Stereoselectivity Inversion by Water Addition in the −SO3H-catalyzed Tandem Prins-Ritter Reaction for Synthesis of 4-amidotetrahydropyran Derivatives",

abstract = "A range of heterogeneous -SO3H 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 (−)-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 4-amidooctahydro-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.",

keywords = "carbon nanotubes, Prins-Ritter reaction, stereoselectivity, sulfonated materials, tetrahydropyran amides, ACID, DIASTEREOSELECTIVE SYNTHESIS, SEQUENCE, CATALYZED PRINS, 3-COMPONENT",

author = "Sidorenko, {Alexander Yu} and Li-Zhulanov, {Nikolai S.} and P{\"a}ivi M{\"a}ki-Arvela and Thomas Sandberg and Kravtsova, {Anna V.} and Peixoto, {Andreia F.} and Cristina Freire and Volcho, {Konstantin P.} and Salakhutdinov, {Nariman F.} and Agabekov, {Vladimir E.} and Murzin, {Dmitry Yu}",

year = "2020",

month = may,

day = "7",

doi = "10.1002/cctc.202000070",

language = "English",

volume = "12",

pages = "2605--2609",

journal = "ChemCatChem",

issn = "1867-3880",

publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

number = "9",

}

RIS

TY - JOUR

T1 - Stereoselectivity Inversion by Water Addition in the −SO3H-catalyzed Tandem Prins-Ritter Reaction for Synthesis of 4-amidotetrahydropyran Derivatives

AU - Sidorenko, Alexander Yu

AU - Li-Zhulanov, Nikolai S.

AU - Mäki-Arvela, Päivi

AU - Sandberg, Thomas

AU - Kravtsova, Anna V.

AU - Peixoto, Andreia F.

AU - Freire, Cristina

AU - Volcho, Konstantin P.

AU - Salakhutdinov, Nariman F.

AU - Agabekov, Vladimir E.

AU - Murzin, Dmitry Yu

PY - 2020/5/7

Y1 - 2020/5/7

N2 - A range of heterogeneous -SO3H 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 (−)-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 4-amidooctahydro-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.

AB - A range of heterogeneous -SO3H 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 (−)-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 4-amidooctahydro-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.

KW - carbon nanotubes

KW - Prins-Ritter reaction

KW - stereoselectivity

KW - sulfonated materials

KW - tetrahydropyran amides

KW - ACID

KW - DIASTEREOSELECTIVE SYNTHESIS

KW - SEQUENCE

KW - CATALYZED PRINS

KW - 3-COMPONENT

UR - http://www.scopus.com/inward/record.url?scp=85082971905&partnerID=8YFLogxK

U2 - 10.1002/cctc.202000070

DO - 10.1002/cctc.202000070

M3 - Article

AN - SCOPUS:85082971905

VL - 12

SP - 2605

EP - 2609

JO - ChemCatChem

JF - ChemCatChem

SN - 1867-3880

IS - 9

ER -

ID: 23988933