The Experts below are selected from a list of 1326 Experts worldwide ranked by ideXlab platform
Iwao Hachiya - One of the best experts on this subject based on the ideXlab platform.
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Titanium Tetraiodide-Promoted Tandem Prins Reaction of Alkynes with Acetals: Synthesis of (Z,Z)-1,5-Diiodo-1,3,5-triarylpenta-1,4-dienes.
ChemInform, 2011Co-Authors: Makoto Shimizu, Kanako Okura, Takuya Arai, Iwao HachiyaAbstract:A stereoselective tandem Prins Reaction of acetals (I) with alkynes (II) affords predominantly (Z,Z)-1,5-diiodo-1,3,5-triarylpenta-1,4-dienes (III) in the presence of TiI4.
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Titanium Tetraiodide-promoted Tandem Prins Reaction of Alkynes with Acetals : Synthesis of (Z,Z)-1,5-Diiodo-1,3,5-triarylpenta-1,4-dienes
Chemistry Letters, 2010Co-Authors: Makoto Shimizu, Kanako Okura, Takuya Arai, Iwao HachiyaAbstract:In the presence of titanium tetraiodide, a tandem Prins Reaction of alkynes proceeded with acetals to give (Z,Z)-1,5-diiodo-1,3,5-triarylpenta-1,4-dienes in good yields, where an intriguing reversa...
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aza Prins Reaction promoted by titanium tetraiodide and iodine
Chemistry Letters, 2007Co-Authors: Makoto Shimizu, Toru Baba, Shingo Toudou, Iwao HachiyaAbstract:In the presence of titanium tetraiodide and iodine, olefins and acetylenes underwent aza-Prins Reaction to give 1,3-iodoamines in good yields.
Masami Sakamoto - One of the best experts on this subject based on the ideXlab platform.
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Correction: Highly selective aluminium-catalysed intramolecular Prins Reaction for L-menthol synthesis
RSC Advances, 2015Co-Authors: Hisanori Itoh, Hironori Maeda, Shinya Yamada, Yoji Hori, Takashi Mino, Masami SakamotoAbstract:Correction for ‘Highly selective aluminium-catalysed intramolecular Prins Reaction for L-menthol synthesis’ by H. Itoh et al., RSC Adv., 2014, 4, 61619–61623.
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Highly selective aluminium-catalysed intramolecular Prins Reaction for L-menthol synthesis
RSC Adv., 2014Co-Authors: Hisanori Itoh, Hironori Maeda, Shinya Yamada, Yoji Hori, Takashi Mino, Masami SakamotoAbstract:An aluminium complex bearing 2-cyclohexyl-6-phenylphenol afforded (5R)-n-isopulegol from (R)-citronellal via the intermolecular Prins Reaction with an exceptionally high diastereoselectivity. Using this Reaction, L-menthol was obtained with an excellent diastereoselectivity.
R. F. Talipov - One of the best experts on this subject based on the ideXlab platform.
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Influence of the Pore Diameter in Zeolites on the Activation Energy of Formation of 4-Alkyl-1,3-Dioxanes in the Prins Reaction
Kinetics and Catalysis, 2019Co-Authors: I. V. Vakulin, R. F. Talipov, G. R. Talipova, P. A. Pas’ko, O. Yu. KupovaAbstract:Using the dependence of the activation energy of 4-alkyl-1,3-dioxane formation on the pore diameter of zeolites, the catalytic activity of the latter in the Prins Reaction was theoretically explained. The stabilization of a preReaction π-complex in the cavities of a number of zeolites ( $${\text{Na}}_{x}^{ + }$$ (H_2O)_ y )[Al_ a Si_ b O_ c ], Al_ a P_ b O_ c , and Ca_ x [H_2O]_ y Al_ a Si_ b O_ c ) is studied by molecular dynamics methods. It is shown that the dependence of the stabilization energy of the π-complex and the transition state on the diameter of the cavity has an extremal shape. Taking into account the stabilization energies of the π-complex and the transition state in the zeolite cavity, the change in the activation energy of the 4-alkyl-1,3-dioxane formation is determined depending on the pore size. A comparison is made of the nature of changes in the transition state stabilization energy and the activation energy of the cavity diameter. It is demonstrated that the dependence of the activation energy on the diameter gives a narrower interval of optimal pore sizes.
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Theoretical investigation of the role of formaldehyde dimers in the Prins Reaction
Reaction Kinetics Mechanisms and Catalysis, 2013Co-Authors: O. Yu. Kupova, I. V. Vakulin, R. F. Talipov, N. D. Morozkin, G. R. TalipovaAbstract:Some features of adding a formaldehyde dimer to alkenes by the Prins Reaction with the formation of oxygen-containing heterocycles are studied at the MP2(fc)/6-31G(d) computational level. The structure of the transition states and key intermediates are established, and thermochemical Reaction parameters are determined. It is shown that this interaction in the gas phase or nonpolar media with the formation of 1,3-dioxanes is a single-stage pseudo synchronous syn-addition. Alkyl substituents at the double bond reduce activation energy. It is revealed that the hydrogenated pyrans formation by the Prins Reaction is possible not only with the participation of formaldehyde monomers, but with its oligomers either. However, the activation energy of this Reaction is higher than that of 1,3-dioxane formation.
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A theoretical investigation of the Reaction mechanism for hydrogenated furan formation under Prins Reaction conditions in trifluoroacetic acid medium
Reaction Kinetics Mechanisms and Catalysis, 2013Co-Authors: Raulia R. Syrlybaeva, I. V. Vakulin, R. F. TalipovAbstract:The formation mechanism of hydrogenated furans by coupling between terminal alkenes and aldehydes in trifluoroacetic acid medium were investigated by ab initio calculations, the main attention was focused on the study of the rate controlling step. Two possible mechanisms for this Reaction involving unsaturated alkoxycarbenium ions or dioxolenium ions as a key intermediate were considered. It was shown that the mechanism of formation of 3-alkylsubstituted hydrogenated furans in trifluoroacetic acid under Prins Reaction conditions preferably includes recyclization of 3-(2-hydroxyethyl)-1-trifluoromethyl-2,5-dioxolenium ions.
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Transformation of betulin diacetate by the Prins Reaction
Russian Journal of Bioorganic Chemistry, 2008Co-Authors: A. V. Rybina, R. F. Talipov, I. S. Shepelevich, F. Z. Galin, L. V. SpirikhinAbstract:The interaction of betulin diacetate with formaldehyde by the Prins Reaction in various media was studied. As a result, 3β,28-di- O -acetyl-30-hydroxymethyl-(20)29-lupene, 3β-acetyl-28-hydroxy-(20)29-lupene, and 3β,28-di- O -acetoxy-19-(5′,6′-dihydro-2′ H -pyran-4′-yl)-20,29,30-trinorlupane were obtained.
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Transformation of betulin diacetate by the Prins Reaction
Bioorganicheskaia khimiia, 2008Co-Authors: A. V. Rybina, R. F. Talipov, I. S. Shepelevich, F. Z. Galin, L. V. SpirikhinAbstract:The interaction of betulin diacetate with formaldehyde by the Prins Reaction in various media was studied. As a result, 3beta,28-di-O-acetyl-30-hydroxymethyl-(20)29-lupene, 3beta-acetyl-28-hydroxy-(20)29-lupene, and 3beta,28-di-O-acetoxy-19-(5',6'-dihydro-2'H-pyran-4'-yl)-20,29,30-trinorlupane were obtained.
Michael B. Hursthouse - One of the best experts on this subject based on the ideXlab platform.
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on the choice of lewis acids for the Prins Reaction two total syntheses of civet
Tetrahedron, 2011Co-Authors: Freda K I Chio, Simon J. Coles, Michael B. Hursthouse, Julie Warne, Damien Gough, Mark J Penny, Sasa Green, Peter Jones, Lorraine A Hassall, Thomas M McguireAbstract:While developing new variations of the Prins cyclisation Reaction, the effect of the choice of Lewis acid on the outcome of the Reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation Reaction of homoallylic alcohols, and two new modifications of the Reaction: the triflate-trapped Prins adduct and the Mukaiyama–Aldol–silyl-Prins Reaction. Two of these methods are employed in two complementary total syntheses of the important perfumery compound, (±)-Civet.
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On the choice of Lewis acids for the Prins Reaction; two total syntheses of (±)-Civet
Tetrahedron, 2011Co-Authors: Freda K I Chio, Simon J. Coles, Michael B. Hursthouse, Julie Warne, Damien Gough, Mark J Penny, Sasa Green, Peter Jones, Lorraine A Hassall, Thomas M McguireAbstract:While developing new variations of the Prins cyclisation Reaction, the effect of the choice of Lewis acid on the outcome of the Reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation Reaction of homoallylic alcohols, and two new modifications of the Reaction: the triflate-trapped Prins adduct and the Mukaiyama–Aldol–silyl-Prins Reaction. Two of these methods are employed in two complementary total syntheses of the important perfumery compound, (±)-Civet.
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A detailed investigation of the aza-Prins Reaction
Organic & Biomolecular Chemistry, 2010Co-Authors: Adrian P. Dobbs, Sebastien J. J. Guesné, Robert J. Parker, John Skidmore, Richard A. Stephenson, Michael B. HursthouseAbstract:The development of a Lewis acid-promoted aza-Prins Reaction to form piperidines and pyrrolidines is described. Indium trichloride has been found to be a highly successful and mild Lewis acid for promoting this Reaction. A thorough mechanistic investigation is described, including the factors that influence the formation of the 5- or 6-membered ring product(s).
Makoto Shimizu - One of the best experts on this subject based on the ideXlab platform.
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Titanium Tetraiodide-Promoted Tandem Prins Reaction of Alkynes with Acetals: Synthesis of (Z,Z)-1,5-Diiodo-1,3,5-triarylpenta-1,4-dienes.
ChemInform, 2011Co-Authors: Makoto Shimizu, Kanako Okura, Takuya Arai, Iwao HachiyaAbstract:A stereoselective tandem Prins Reaction of acetals (I) with alkynes (II) affords predominantly (Z,Z)-1,5-diiodo-1,3,5-triarylpenta-1,4-dienes (III) in the presence of TiI4.
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Titanium Tetraiodide-promoted Tandem Prins Reaction of Alkynes with Acetals : Synthesis of (Z,Z)-1,5-Diiodo-1,3,5-triarylpenta-1,4-dienes
Chemistry Letters, 2010Co-Authors: Makoto Shimizu, Kanako Okura, Takuya Arai, Iwao HachiyaAbstract:In the presence of titanium tetraiodide, a tandem Prins Reaction of alkynes proceeded with acetals to give (Z,Z)-1,5-diiodo-1,3,5-triarylpenta-1,4-dienes in good yields, where an intriguing reversa...
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aza Prins Reaction promoted by titanium tetraiodide and iodine
Chemistry Letters, 2007Co-Authors: Makoto Shimizu, Toru Baba, Shingo Toudou, Iwao HachiyaAbstract:In the presence of titanium tetraiodide and iodine, olefins and acetylenes underwent aza-Prins Reaction to give 1,3-iodoamines in good yields.
