Category: 329735-68-4

《Chiral Organomagnesiates as Dual Reagents for Bromine-Magnesium Exchange of 2-Bromopyridine and Access to Chiral α-Substituted 2-Pyridylcarbinols》 was published in European Journal of Organic Chemistry in 2012. These research results belong to Catel, Delphine; Chevallier, Floris; Mongin, Florence; Gros, Philippe C.. Synthetic Route of C24H34O2 The article mentions the following:

Magnesiates generated from butyllithium, butylmagnesium chloride, and racemic or nonracemic diols such as rac-BINOL or (R,R)-TADDOL chemoselectively metalated 2-bromopyridine; reaction of the intermediate metalated pyridine with aldehydes yielded α-substituted 2-pyridinemethanols chemoselectively in 58-85% yields. Using a magnesiate derived from (R,R)-TADDOL, dibutylmagnesium, and butyllithium, 2-bromopyridine underwent enantioselective metal-bromine exchange and addition to 4-methoxybenzaldehyde to give α-(4-methoxyphenyl)-2-pyridinemethanol in 28% yield and in 76% ee. In addition to this study using (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol, there are many other studies that have used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Synthetic Route of C24H34O2) was used in this study.

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Synthetic Route of C24H34O2 The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2010,Angewandte Chemie, International Edition included an article by Liu, Taifeng; Liu, Yan; Xuan, Weimin; Cui, Yong. Application In Synthesis of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol. The article was titled 《Chiral nanoscale metal-organic tetrahedral cages: diastereoselective self-assembly and enantioselective separation》. The information in the text is summarized as follows:

Chiral atropisomeric 1,1′-biphenyl-3,3-diyl-bridged 1,3-diketones and their iron(III) and gallium complexes undergo self-assembly yielding tetrahedral homochiral clusters possessing chiral cavity; alcs. were resolved by formation of host-guest compounds with the iron(III) cluster tris-diketonate. Diacetylation of (1S)- and (1R)-5,5′,6,6′-tetramethyl-2,2′-(OMOM)2-1,1′-biphenyl-3,3′-dicarboxaldehyde [3,3′-Q(CHO)2] by biacetyl-trimethyl phosphite complex gave the enantiopure bis-diketonate proligands, 3,3′-Q[CH(COMe)2]2. These ligands were reacted with FeCl3 and GaCl3 giving the corresponding tetrameric nanoscale complex hosts, [Fe[3,3′-Q[C(COMe)2]2]3]4 (1) and [Ga[3,3′-Q[C(COMe)2]2]3]4 (2), composed from homochiral ΔΔΔΔ- or ΛΛΛΛ-units, for ligands (1R)- and (1S)-3,3′-Q[CH(COMe)2]2, resp. Inclusion of racemic 2-butanol and 3-methyl-2-butanol into chiral cavity of (1S)-1 with subsequent desorption gave the corresponding resolved alcs. with >99% ee. After reading the article, we found that the author used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Application In Synthesis of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).Application In Synthesis of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The author of 《Total synthesis of indolizidine alkaloid (-)-209D: overriding substrate bias in the asymmetric rhodium-catalyzed [2+2+2] cycloaddition》 were Yu, Robert T.; Lee, Ernest E.; Malik, Guillaume; Rovis, Tomislav. And the article was published in Angewandte Chemie, International Edition in 2009. Recommanded Product: 329735-68-4 The author mentioned the following in the article:

The use of chiral biphenyl-based phosphoramidite ligands on rhodium provides an efficient [2+2+2] cycloaddition between terminal alkyl alkynes, e.g. 1-octyne, and alkenyl isocyanates, e.g. H2C:CH(CH2)3NCO. The cycloaddition proceeds through a CO migration pathway, and facilitates a rapid four-step asym. synthesis of indolizidine (-)-209D (I). In the experiment, the researchers used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Recommanded Product: 329735-68-4)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Recommanded Product: 329735-68-4 The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diolOn October 18, 2004 ,《Synthesis and characterization of alkyllanthanum biphenolate complexes as catalysts for hydroamination/cyclization and hydrosilylation》 was published in European Journal of Inorganic Chemistry. The article was written by Gribkov, Denis V.; Hampel, Frank; Hultzsch, Kai C.. The article contains the following contents:

The homochiral, dimeric biphenolate alkyllanthanum complex [La{(R)-Biphen}{CH(SiMe3)2}]2 can be prepared by facile alkane elimination starting from [La{CH(SiMe3)2}3] and enantiopure (R)-3,3′-di-tert-butyl-5,5′,6,6′-tetramethyl-1,1′-biphenyl-2,2′-diol [H2{(R)-Biphen}]. Single-crystal x-ray diffraction revealed that the two La{(R)-Biphen}{CH(SiMe3)2} fragments are connected through bridging phenolate groups of the biphenolate ligands. The two different phenolate groups undergo an intramol. exchange process in solution leading to their equivalence on the NMR time scale. The biphenolate alkyl complex shows high catalytic activity for hydroamination/cyclization of aminoalkenes, similar to previously known lanthanocene catalysts, but only low enantio-selectivity. Addition of THF to [La{(R)-Biphen}{CH(SiMe3)2}]2 leads to a monomeric tris-THF adduct [La{(R)-Biphen}{CH(SiMe3)2}(THF)3] with higher catalytic activity than the THF-free homochiral dimer in the cyclization of 2,2-dimethylpent-4-enylamine, suggesting that the dimeric structure of the catalyst system prevails under catalytic conditions in the absence of THF. Addition of HN(SiHMe2)2 to [La{(R)-Biphen}{CH(SiMe3)2}(THF)3] results in the formation of [La{(R)-Biphen}{N(SiHMe2)2}(THF)3] which is in equilibrium with its homochiral dimer [La{(R)-Biphen}{N(SiHMe2)2}(THF)]2 at elevated temperatures The biphenolate alkyl complexes exhibit good catalytic activity and diastereoselectivity in the hydrosilylation of styrene. Hydrosilylation of 1-hexene and norbornene also proceeds with high diastereoselectivity but rather low activity. In the part of experimental materials, we found many familiar compounds, such as (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Reference of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Reference of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Gutierrez, Elisa G.; Moorhead, Eric J.; Smith, Eva H.; Lin, Vivian; Ackerman, Laura K. G.; Knezevic, Claire E.; Sun, Victoria; Grant, Sharday; Wenzel, Anna G. published an article in European Journal of Organic Chemistry. The title of the article was 《Electron-Withdrawing, Biphenyl-2,2′-diol-Based Compounds for Asymmetric Catalysis》.Application of 329735-68-4 The author mentioned the following in the article:

Facile synthetic routes to a chiral chloro-substituted biphenyl-2,2′-diyl hydrogen phosphate and a chiral O,O-biphenyl-2,2′-diyl phosphoramidothioate are described. The performance of these compounds as catalysts for the hydrophosphonylation of N-(2-methoxyphenyl) benzaldimine and the Friedel-Crafts alkylation of indole with chalcone was investigated. In the latter reaction, the chloro-substituted phosphoric acid derivative was found to rival the best Bronsted acid catalysts reported to date. The results came from multiple reactions, including the reaction of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Application of 329735-68-4)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).Application of 329735-68-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Hultzsch, Kai C.; Jernelius, Jesper A.; Hoveyda, Amir H.; Schrock, Richard R. published an article on February 15 ,2002. The article was titled 《The first polymer-supported and recyclable chiral catalyst for enantioselective olefin metathesis》, and you may find the article in Angewandte Chemie, International Edition.Quality Control of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The information in the text is summarized as follows:

The synthesis of polymer-bound [(1R)-3,3′-Bis(1,1-dimethylethyl)-6,6′-tetramethyl[1,1′-biphenyl]-2,2′-diolato(2-)-κO,κO’][2,6-bis(1-methylethyl)benzenaminato(2-)](2-methyl-2-phenylpropylidene)molybdenum (I) from [2,6-bis(1-methylethyl)benzenaminato(2-)][1,2-di(methoxy-κO)ethane](2-methyl-2-phenylpropylidene)bis(trifluoromethanesulfonato-κO)molybdenum and a chiral polymer-bound [1,1′-biphenyl]-2,2′-diol precursor was reported. The activity of the polymer-bound catalyst I was compared to un-supported [(1R)-3,3′-bis(1,1-dimethylethyl)-5,5′,6,6′-tetramethyl[1,1′-biphenyl]-2,2′-diolato(2-)-κO,κO’][2,6-bis(1-methylethyl)benzenaminato(2-)](2-methyl-2-phenylpropylidene)molybdenum in metathesis reactions of several alkenes. After reading the article, we found that the author used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Quality Control of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Quality Control of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Ogasawara, Masamichi; Watanabe, Susumu; Nakajima, Kiyohiko; Takahashi, Tamotsu published an article on February 24 ,2010. The article was titled 《Enantioselective synthesis of planar-chiral phosphaferrocenes by molybdenum-catalyzed asymmetric interannular ring-closing metathesis》, and you may find the article in Journal of the American Chemical Society.Safety of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The information in the text is summarized as follows:

Planar-chiral nonracemic phosphaferrocenophanes I [2a-f; a, R = H, R1 = H, X-X = (CH2)4, Z = CH2; b, R = Me, R1 = H, X-X = (CH2)4, Z = CH2; c, R = Me, R1 = Me, X-X = (CH2)4, Z = CH2; d, R = Me, R1 = H, X-X = CH2OCH2, Z = CH2; e, R = Me, R1 = H, X-X = (CH2)5, Z = CH2; f, R = Me, R1 = H, X-X = (CH2)4, Z = CH2CH2] were prepared by asym. ring-closing metathesis of the corresponding precursors, [[η5-3,4-X2-2,5-(CH2:CRCH2)2C5](η5-C5R14ZCH:CH2)Fe] (1a-f), catalyzed by chiral BINOL molybdenum(IV) carbene-imido complexes [(Ln)Mo:CHCMe2Ph(DippN)] [Mo-1-Mo-3, L1 = (R)-3,3′-tBu2-1,1′-octahydrobinaphthalene-2,2′-diolato, L2 = (R)-3,3′-[3,5-(CF3)2C6H3]2-1,1′-binaphthalene-2,2′-diolato, L3 = (R)-3,3′-[2,5-(CF3)2C6H3]2-1,1′-binaphthalene-2,2′-diolato]. Enantioselective synthesis of planar-chiral phosphaferrocenes was realized for the first time by molybdenum-catalyzed asym. ring-closing metathesis (ARCM) in up to 99% ee, which is the first application of ARCM to induction of chirality in mols. devoid of stereogenic centers. After reading the article, we found that the author used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Safety of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Safety of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

《Kinetic Resolution of Planar-Chiral (η6-Arene)Chromium Complexes by Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis》 was published in Angewandte Chemie, International Edition in 2012. These research results belong to Ogasawara, Masamichi; Wu, Wei-Yi; Arae, Sachie; Watanabe, Susumu; Morita, Tomotaka; Takahashi, Tamotsu; Kamikawa, Ken. Related Products of 329735-68-4 The article mentions the following:

Authors have developed an effective method for the kinetic resolution of racemic planar-chiral (η6-arene)chromium complexes by Mo-catalyzed asym. ring-closing metathesis. After the appropriate derivatization, the obtained optically active (diphenylphosphinoarene)chromium complex can be utilized as an excellent chiral ligand in Rh-catalyzed asym. reactions. In the experiment, the researchers used many compounds, for example, (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Related Products of 329735-68-4)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Related Products of 329735-68-4 The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts