Later on, Prins reaction emerged as a powerful C-O and C-C bond forming technique in the synthesis of various molecules in organic synthesis. (wikipedia.org)
2017 ) Total Synthesis of (+)-Lophirone H and Its Pentamethyl Ether Utilizing an Oxonium-Prins Cyclization. (academictree.org)
The Prins cyclization of styrene (SE) with paraformaldehyde (PFCHO) was conducted with mesoporous ZnAlMCM-41 catalysts for the synthesis of 4-phenyl-1,3-dioxane (4-PDO) using a liquid phase heterogeneous catalytic method. (iith.ac.in)
Since ZnAlMCM-41(75) has higher catalytic activity than other solid acid catalysts, washed ZnAlMCM-41(75)/W-ZnAlMCM-41(75) was prepared using an efficient chemical treatment method and used with various reaction parameters to find an optimal parameter for the highly selective synthesis of 4-PDO. (iith.ac.in)
W-ZnAlMCM-41(75) was also used in the Prins cyclization of olefins with PFCHO and formalin (FN, 37% aqueous solution of formaldehyde (FCHO)) under different reaction conditions to obtain 1,3-dioxanes, which are widely used as solvents or intermediates in organic synthesis. (iith.ac.in)
Also, camphor sulfonic acid (CSA) is achieving enormous significance in organic synthesis, as this catalyst is used in the synthesis of chromans, ligands, and pseudo glycosides, as an auxiliary and in some polymerization reactions [8]. (lupinepublishers.com)
So far, to the best of our knowledge, there is no report available on the use of camphor sulfonic acid as an organ catalyst for the synthesis of highly substituted Piperidines. (lupinepublishers.com)
C . Y . Chen, W . P . Hu, M . C . Liu, P. C. Yan , and J. J. Wang *, M. I. Chung , "Efficient Synthesis of Quinazoline s with Hypervalent Iodine as a Catalyst", Tetrahedron 201 3 , 69 , 9735-9741. (kmu.edu.tw)
Reaction9
The Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile or elimination of an H+ ion. (wikipedia.org)
The early studies on Prins reaction are exploratory in nature and did not attract much attention until 1937. (wikipedia.org)
Many variations of the Prins reaction exist because it lends itself easily to cyclization reactions and because it is possible to capture the oxo-carbenium ion with a large array of nucleophiles. (wikipedia.org)
The halo-Prins reaction is one such modification with replacement of protic acids and water by lewis acids such as stannic chloride and boron tribromide. (wikipedia.org)
The Prins-pinacol reaction is a cascade reaction of a Prins reaction and a pinacol rearrangement. (wikipedia.org)
2019 ) Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes - a reaction at the 'oxonium-Prins' '-quinone methide cycloaddition' mechanistic nexus. (academictree.org)
For a comparison study, the Prins cyclization reaction was also conducted over different nanoporous catalysts,e.g.mesoporous solid acid catalysts, AlMCM-41(21) and ZnMCM-41(21), and microporous catalysts, USY, Hβ, HZSM-5, and H-mordenite. (iith.ac.in)
The recyclable mesoporous ZnAlMCM-41 catalysts were reused in this reaction to evaluate their catalytic stabilities. (iith.ac.in)
Based on the nature of catalysts used under different reaction conditions, a reasonable plausible reaction mechanism for the Prins cyclization of SE with PFCHO is proposed. (iith.ac.in)
20171
2017 ) 3d/4f Coordination Clusters as Cooperative Catalysts for Highly Diastereoselective Michael Addition Reactions. (academictree.org)
Styrene1
The original reactants employed by Dutch chemist Hendrik Jacobus Prins [de] in his 1919 publication were styrene (scheme 2), pinene, camphene, eugenol, isosafrole and anethole. (wikipedia.org)
Tetrahydrofurans1
List, B. Catalytic Asymmetric Vinylogous Prins Cyclization: A Highly Diastereo- and Enantioselective Entry to Tetrahydrofurans. (mpg.de)
Organic2
Hendrik Jacobus Prins discovered two new organic reactions during his doctoral research in the year of 1911-1912. (wikipedia.org)
Search of an efficient organ catalyst for organic transformations remain a challenging task. (lupinepublishers.com)
Catalytic4
Notably, it can be seen from the catalytic results of all catalysts that the W-ZnAlMCM-41(75) catalyst has higher 4-PDO selectivity with exceptional catalytic activity than other microporous and mesoporous catalysts. (iith.ac.in)
A cooperative catalytic process through Palladium and Brønsted acid activation has been developed for the conjugate addition of cyclic ß -keto esters 2 to azoalkenes 1 directly followed by hemiaminal formation upon cyclization. (uni-leipzig.de)
We report herein the catalytic asymmetric cyclization of 1-aryl terpenols to afford enantiomerically highly enriched cis-tetrahydrocannabinoid scaffolds in a single step. (uni-leipzig.de)
2022 ) Recent progress in asymmetric synergistic catalysis - the judicious combination of selected chiral aminocatalysts with achiral metal catalysts. (academictree.org)
This transformation was enabled by utilizing chiral Pd-aqua complexes as combined Brønsted acid-base catalysts. (uni-leipzig.de)
As powerful chiral catalysts, strongly acidic imidodiphosphorimidates (IDPis) have been identified, which furnish the products with good yields and excellent enantioselectivity. (uni-leipzig.de)
Based upon their exceptional reactivity as cooperative Brønsted acid-base catalysts, chiral diphosphane Pd-aqua complexes have successfully been utilized in a broad range of asymmetric transformations. (uni-leipzig.de)
Originally discovered by Sodeoka 25 years ago, they readily form reactive chiral Pd enolates upon deprotonation of b-dicarbonyl compounds and simultaneously, a Brønsted acid liberated from the catalyst activates the electrophile. (uni-leipzig.de)
We report herein an asymmetric cooperative process for the enantioselective 1,6-addition of β-ketoesters to in situ generated para-quinone methides with chiral Pd−aqua complexes as mixed Brønsted acid−base catalysts. (uni-leipzig.de)
Results1
With lewis acid stannic chloride the oxonium ion is activated and the pinacol rearrangement of the resulting Prins intermediate results in ring contraction and referral of the positive charge to the TIPS ether which eventually forms an aldehyde group in the final product as a mixture of cis and trans isomers with modest diastereoselectivity. (wikipedia.org)
Synthesis1
Later on, Prins reaction emerged as a powerful C-O and C-C bond forming technique in the synthesis of various molecules in organic synthesis. (wikipedia.org)
Reactions6
Hendrik Jacobus Prins discovered two new organic reactions during his doctoral research in the year of 1911-1912. (wikipedia.org)
Many variations of the Prins reaction exist because it lends itself easily to cyclization reactions and because it is possible to capture the oxo-carbenium ion with a large array of nucleophiles. (wikipedia.org)
This methodology highlights the use of simple starting materials and commercially available aqueous perrhenic acid as a catalyst for Prins cyclization reactions to directly synthesize 2,6-disubstituted tetrahydropyran-4-ones. (bvsalud.org)
Moreover, the palladium catalyst was also used extensively in cross-coupling reactions, such as Buchwald-Hartwig, Suzuki-Miyaura, Heck, Sonogashira, Negishi, and Stille to synthesize a variety of useful compounds [ 17 ] [ 18 ] . (encyclopedia.pub)
The editors have included state-of-the-art strategies, including transition-metal reactions involving unsaturated systems (reactions of allenes, new gold(I)-catalyzed reactions, and Prins reaction). (elsevier.com)
Besides dimerization reactions, isomerization was also observed on these catalysts. (go.jp)
Zeolite1
The highest yield of the desired product (55.4%) was achieved over a zeolite catalyst possessing moderate acidity, developed mesoporosity (V meso 0.60 cm 3 /g) and a high external surface area (290 m 2 /g). (abo.fi)
Acid2
With lewis acid stannic chloride the oxonium ion is activated and the pinacol rearrangement of the resulting Prins intermediate results in ring contraction and referral of the positive charge to the TIPS ether which eventually forms an aldehyde group in the final product as a mixture of cis and trans isomers with modest diastereoselectivity. (wikipedia.org)
A new variation of Prins cyclization to directly and stereoselectively synthesize cis-2,6-disubstituted tetrahydropyran-4-ones from 3-chlorohomoallylic alcohols and aldehydes catalyzed by perrhenic acid is reported. (bvsalud.org)
Commercially1
The obtained catalysts were investigated in the Prins cyclization of isovaleraldehyde with isoprenol yielding a commercially valuable tetrahydropyranol (Florol). (abo.fi)
Scheme2
The original reactants employed by Dutch chemist Hendrik Jacobus Prins [de] in his 1919 publication were styrene (scheme 2), pinene, camphene, eugenol, isosafrole and anethole. (wikipedia.org)
The cyclization of certain allyl pulegones in scheme 7 with titanium tetrachloride in dichloromethane at −78 °C gives access to the decalin skeleton with the hydroxyl group and chlorine group predominantly in cis configuration (91% cis). (wikipedia.org)
Research1
In this research, the palladium catalyst was employed to complete the bridge between C3 and C4. (encyclopedia.pub)