Month: February 2023

Catalytic asymmetric cycloetherification via intramolecular oxy-Michael addition of enols was written by Murata, Ryuichi;Asano, Keisuke;Matsubara, Seijiro. And the article was included in Tetrahedron in 2021.Reference of 1256245-79-0 This article mentions the following:

In this study, the asym. cycloetherification of enols were presented, which were generated in situ from enone-bearing ketones, using chiral bifunctional organocatalysts bearing amino and squaramide groups. This transformation chemo- and enantioselectively afforded dihydropyran derivatives I [R¹ = Ph, 4-BrC₆H₄, 2-naphthyl, etc.; R² = CF₃, CF₂Br, CO₂Et, Ph; R³ = H, C(O)Ph], which were the core structures of building blocks for synthesizing glycans. In the experiment, the researchers used many compounds, for example, 3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0Reference of 1256245-79-0).

3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0) belongs to quinuclidine derivatives.The reactions of quinuclidine compounds that lead to opening of the 1-azabi-cyclic system at the N-C and C-C bonds to give piperidine derivatives or, via subsequent rearrangements, derivatives of other heterocyclic systems, are correlated. Processes involving the fragmentation of quinuclidines in chemical reactions and under electron impact and reactions involving expansion of the quinuclidine ring and intermediate cleavage of the bicyclic system are examined.聽 Asymmetric construction of quinuclidine derivatives has been realized by an iridium-catalyzed allylic dearomatization reaction. The catalytic system, derived from [Ir(cod)Cl]2 and the Feringa ligand, tolerates a broad range of substrates. A large array of quinuclidine derivatives can be obtained under mild conditions in good to excellent yields (68%鈥?6%), diastereoselectivity (up to >20/1 dr), and enantioselectivity (up to >99% ee).Reference of 1256245-79-0

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Stereoselective synthesis of epoxyisoprostanes: an organocatalytic and “pot-economy” approach was written by Weng, Jiang;Wang, Sheng;Huang, Lin-Jie;Luo, Zhang-Yi;Lu, Gui. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2015.Electric Literature of C26H29ClN2O This article mentions the following:

An efficient and direct synthetic route to epoxyisoprostane EC Me ester (I) has been accomplished in 8 steps (10% overall yield) from readily available starting materials using a series of asym. organocatalytic reactions and one-pot operations. In the experiment, the researchers used many compounds, for example, (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3Electric Literature of C26H29ClN2O).

(1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3) belongs to quinuclidine derivatives. Quinuclidine derivatives are also widely utilized as homogeneous or heterogeneous catalysts in various asymmetric processes such as Morita鈥揃aylis鈥揌illman reactions, Sharpless dihydroxylation reactions, and phase-transfer catalytic reactions. As a ligand, quinuclidine is useful in the studies of OsO4-catalyzed dihydroxylation of olefins. It plays an important role in the formation of onium salts used testing of PAC-antagonist activity.Electric Literature of C26H29ClN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Polymeric pseudo-liquid membranes from poly(octadecyl methacrylate) was written by Tsujimoto, Hiroki;Yoshikawa, Masakazu. And the article was included in Journal of Membrane Science in 2013.SDS of cas: 200132-54-3 This article mentions the following:

The novel liquid membrane system, which is named polymeric pseudo-liquid membrane, was constructed from poly(octadecyl methacrylate) (PC18MA), which showed a rubbery state under operating conditions, as a membrane matrix, and dibenzo-18-crown-6 (DB18C6) for the transport of KCl or O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (AAMC) for that of racemic mixture of phenylglycine (Phegly) as a carrier. The results of KCl transport revealed that KCl transport was attained by carrier-diffusion mechanism even though membrane matrix was composed of polymeric material. The polymeric pseudo-liquid membrane containing chiral carrier AAMC showed optical resolution ability, in other words, the membrane selectively transported L-Phegly and its permselectivity toward L-Phegly reached 1.48 at the operating temperature of 40 掳C. Chiral separation ability was greatly dependent on the operating temperature and a wide range of permselectivity from L-isomer to D-isomer permselectivity was attained by adjusting the operating temperature The present study revealed that the polymeric pseudo-liquid membrane is a promising membrane system in membrane separation In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3SDS of cas: 200132-54-3).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. It is employed to prepare quinine and alkaloids. Carbamoyl boranes are generally prepared as adducts with tertiary amines, such as trialkyl amines, pyridine, or quinuclidine, via two synthetic approaches based either on amidation of amine-carboxyborane adducts or on hydrolysis of amine-cyanoboranes.SDS of cas: 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Enantioselective Synthesis of Benzofuran-Fused N-Heterocycles via Chiral Squaramide Catalyzed [4 + 2] Cyclization of Azadienes with Azlactones was written by Li, Xiaoping;Yan, Juzhang;Qin, Jialiang;Lin, Shilin;Chen, Weiwen;Zhan, Ruoting;Huang, Huicai. And the article was included in Journal of Organic Chemistry in 2019.Quality Control of 3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione This article mentions the following:

An asym. cyclization reaction of azadienes and azlactones was investigated by employing a Cinchona squaramide catalyst, which could afford a series of benzofuran-fused six-membered heterocycles containing a 伪,伪-disubstituted amino acid unit in a highly diastereoselective (>20:1 dr) and enantioselective (up to 99% ee) manner with good to excellent yields (up to 92%). A plausible pathway was proposed to explain the reaction process. In the experiment, the researchers used many compounds, for example, 3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0Quality Control of 3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione).

3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0) belongs to quinuclidine derivatives. In alkane solvents quinuclidine is a Lewis base that forms adducts with a variety of Lewis acids. Traditionally, quinuclidine scaffolds can be constructed by second-order nucleophilic substitution (SN2) reaction or condensation reaction of piperidine derivatives. However, most of these reactions are racemic or chiral auxiliary-assisted processes.Quality Control of 3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Nucleophilic enantioselective synthesis of 6-fluoro-L-dopa via chiral catalytic phase-transfer alkylation was written by Tang, Ganghua;Tang, Xiaolan;Zhang, Lan;Wang, Yongxian. And the article was included in Zhongguo Yaowu Huaxue Zazhi in 2002.Formula: C37H37BrN2O This article mentions the following:

6-Fluoro-L-dopa was synthesized from 6-nitropiperonal via nucleophilic fluorination, reductive iodination, chiral catalytic phase-transfer alkylation, and hydrolysis reactions. The enantiomeric purity of 6-fluoro-L-dopa was determined by HPLC method using a chiral mobile phase and reversed-phase C₁₈ column. The overall yield from 6-nitropiperonal was 38%, and enantiomeric purity of 6-fluoro-L-dopa was above 95%. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Formula: C37H37BrN2O).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine is found as a structural component of some biomolecules including quinine. The reactions of quinuclidine compounds that lead to opening of the 1-azabi-cyclic system at the N-C and C-C bonds to give piperidine derivatives or, via subsequent rearrangements, derivatives of other heterocyclic systems, are correlated.Formula: C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Organocatalytic Regio- and Asymmetric C-Selective S_NAr Reactions-Stereoselective Synthesis of Optically Active Spiro-pyrrolidone-3,3′-oxoindoles was written by Bella, Marco;Kobbelgaard, Sara;Jorgensen, Karl Anker. And the article was included in Journal of the American Chemical Society in 2005.Product Details of 200132-54-3 This article mentions the following:

The first example of catalytic enantioselective nucleophilic aromatic substitution of 尾-dicarbonyl compounds is presented. An O-benzoylated cinchona alkaloid derivative catalyst gave a selective C-arylation reaction compared to, e.g., the corresponding benzylated catalyst which provided a 1:1 mixture of the C- and O-arylation products. The reaction proceeds well for various aromatic compounds with different 1,3-dicarbonyl compounds, and the optically active products are obtained in very high yields and with up to 92% ee. One further scope of this reaction is demonstrated by the synthesis of the optically active spiro-pyrrolidone-3,3′-oxoindole structure. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Product Details of 200132-54-3).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine is found as a structural component of some biomolecules including quinine. Carbamoyl boranes are generally prepared as adducts with tertiary amines, such as trialkyl amines, pyridine, or quinuclidine, via two synthetic approaches based either on amidation of amine-carboxyborane adducts or on hydrolysis of amine-cyanoboranes.Product Details of 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Chiral-Squaramide-Catalyzed Sulfa-Michael/Aldol Cascade Reactions for Asymmetric Synthesis of Spirothiochromanones was written by Zhao, Bo-Liang;Du, Da-Ming. And the article was included in Asian Journal of Organic Chemistry in 2015.Synthetic Route of C32H28F6N4O3 This article mentions the following:

In the presence of a quinidine-derived squaramide, arylmethyleneindanones I [R = Ph, 4-FC₆H₄, 2-ClC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 2,4-Cl₂C₆H₃, 2-MeC₆H₄, 4-MeC₆H₄, 2-MeOC₆H₄, 4-MeOC₆H₄, 3,4-(MeO)₂C₆H₃, 3-O₂NC₆H₄, 4-O₂NC₆H₄, 1-naphthyl, 2-thienyl; R¹ = H, Br, Cl; R² = H, Me] underwent diastereoselective and enantioselective sulfa-Michael/aldol cascade reactions with 2-mercaptobenzaldehyde to yield spiroindanethiochromandiones II [R = Ph, 4-FC₆H₄, 2-ClC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 2,4-Cl₂C₆H₃, 2-MeC₆H₄, 4-MeC₆H₄, 2-MeOC₆H₄, 4-MeOC₆H₄, 3,4-(MeO)₂C₆H₃, 3-O₂NC₆H₄, 4-O₂NC₆H₄, 1-naphthyl, 2-thienyl; R¹ = H, Br, Cl; R² = H, Me]. Under analogous conditions, dialkylidenecycloalkanones III (R³ = Ph, 4-BrC₆H₄, 4-MeC₆H₄; X = CH₂, O; Y = bond, CH₂) underwent diastereoselective and enantioselective sulfa-Michael/aldol cascade reactions to yield spirothiochromanones IV (R³ = Ph, 4-BrC₆H₄, 4-MeC₆H₄; X = CH₂, O; Y = bond, CH₂). This organocatalytic cascade reaction provides easy access to highly functionalized spirothiochromanones with three contiguous stereocenters, including one quaternary center, in excellent yields up to 99% with excellent diastereoselectivity up to >99:1. In the experiment, the researchers used many compounds, for example, 3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0Synthetic Route of C32H28F6N4O3).

3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0) belongs to quinuclidine derivatives. Quinuclidine derivatives are also widely utilized as homogeneous or heterogeneous catalysts in various asymmetric processes such as Morita鈥揃aylis鈥揌illman reactions, Sharpless dihydroxylation reactions, and phase-transfer catalytic reactions. The configuration at C-8 (quinuclidine attachment) and C-9 position (bearing hydroxy group) are important as they help in the orientation of hydroxy group and nitrogen atom of quinuclidine.Synthetic Route of C32H28F6N4O3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Total Synthesis of Tryprostatin B: Synthesis and Asymmetric Phase-Transfer-Catalyzed Reaction of Prenylated Gramine Salt was written by Huisman, Matthew;Rahaman, Mizzanoor;Asad, Sharif;Oehm, Sarah;Novin, Sherwin;Rheingold, Arnold L.;Hossain, M. Mahmun. And the article was included in Organic Letters in 2019.SDS of cas: 200132-54-3 This article mentions the following:

A concise and efficient total synthesis of microtubule inhibitor tryprostatin B is described. The key step is the preparation of a diprenylated gramine salt. In this step, the prenyl group is incorporated at the 2-position of the indole moiety by direct lithiation of the Boc-protected gramine. We also developed and optimized the asym. phase-transfer-catalyzed reaction with the diprenylated gramine salt to provide the C2-prenyl tryptophan intermediate resulting in 93% enantiomeric excess (ee) and 65% yield. The total synthesis of tryprostatin B is done in six steps with 35% overall yield. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3SDS of cas: 200132-54-3).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. The development of synthetic approaches for efficient construction of novel quinuclidine derivatives is of great significance. Quinuclidine derivatives can also be formed conveniently by introducing substituents into the quinuclidine ring, but the scope of this method is rather limited by the available source of starting materials.SDS of cas: 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Design and synthesis of chiral hyperbranched polymers containing cinchona squaramide moieties and their catalytic activity in the asymmetric Michael addition reaction was written by Chhanda, Sadia Afrin;Itsuno, Shinichi. And the article was included in Journal of Catalysis in 2019.Electric Literature of C42H44N6O2 This article mentions the following:

Chiral hyperbranched polymers (HBP) containing cinchona alkaloids were synthesized using a Mizoroki-Heck (MH) coupling polymerization reaction between a cinchona squaramide dimer and tri- or tetra-substituted aromatic iodides. This was a new type of polymeric chiral organocatalyst. We found that the as-obtained chiral HBPs show excellent catalytic activity in the asym. Michael reaction. Almost perfect enantioselectivity (>99% ee) was achieved in the reaction of 尾-ketoester and trans-尾-nitrostyrene. The three-dimensional network structure of the chiral HBPs is structurally robust and can be reused for further reaction without any loss in their catalytic activity. In the experiment, the researchers used many compounds, for example, 3,4-Bis(((1S)-quinolin-4-yl((2S)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1204591-50-3Electric Literature of C42H44N6O2).

3,4-Bis(((1S)-quinolin-4-yl((2S)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1204591-50-3) belongs to quinuclidine derivatives.The reactions of quinuclidine compounds that lead to opening of the 1-azabi-cyclic system at the N-C and C-C bonds to give piperidine derivatives or, via subsequent rearrangements, derivatives of other heterocyclic systems, are correlated. Processes involving the fragmentation of quinuclidines in chemical reactions and under electron impact and reactions involving expansion of the quinuclidine ring and intermediate cleavage of the bicyclic system are examined.聽 Asymmetric construction of quinuclidine derivatives has been realized by an iridium-catalyzed allylic dearomatization reaction. The catalytic system, derived from [Ir(cod)Cl]2 and the Feringa ligand, tolerates a broad range of substrates. A large array of quinuclidine derivatives can be obtained under mild conditions in good to excellent yields (68%鈥?6%), diastereoselectivity (up to >20/1 dr), and enantioselectivity (up to >99% ee).Electric Literature of C42H44N6O2

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Cation-Directed Enantioselective N-Functionalization of Pyrroles was written by Armstrong, Roly J.;D’Ascenzio, Melissa;Smith, Martin D.. And the article was included in Synlett in 2016.Reference of 69221-14-3 This article mentions the following:

A catalytic enantioselective N-functionalization of pyrroles has been developed. Imines formed in situ via condensation underwent cation-directed cyclization with complete N-regioselectivity. The cyclized products were obtained with enantiomeric ratios up to 96:4 for aldimine substrates and up to 99:1 for trifluoromethyl ketimines. The reaction proceeds without an acidifying group on the pyrrole and offers a new approach to the generation of chiral nonracemic aminals. In the experiment, the researchers used many compounds, for example, (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3Reference of 69221-14-3).

(1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3) belongs to quinuclidine derivatives. Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. As a ligand, quinuclidine is useful in the studies of OsO4-catalyzed dihydroxylation of olefins. It plays an important role in the formation of onium salts used testing of PAC-antagonist activity.Reference of 69221-14-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider