Category: 851615-07-1

Chiral lithium salts of phosphoric acids as lewis acid-base conjugate catalysts for the enantioselective cyanosilylation of ketones was written by Hatano, Manabu;Ikeno, Takumi;Matsumura, Tokihiko;Torii, Shinobu;Ishihara, Kazuaki. And the article was included in Advanced Synthesis & Catalysis in 2008.Category: alcohols-buliding-blocks The following contents are mentioned in the article:

The catalytic enantioselective cyanosilylation of aromatic ketones was developed by using chiral lithium salts of (R)-BINOL- (BINOL = 2,2′-binaphthol) or (S)-BINAM-derived (BINAM = 2,2′-binaphthamine) phosphoric acid compounds In the presence of 10 mol% of chiral conjugate lithium salts, the corresponding tertiary cyanohydrins were obtained in high yields with moderate to high enantioselectivities. This is the 1st efficient example of asym. catalysis using lithium salts of synthetically useful chiral phosphoric acid compounds A possible catalytic mechanism and transition states are also discussed as a preliminary working hypothesis. This study involved multiple reactions and reactants, such as (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol (cas: 851615-07-1Category: alcohols-buliding-blocks).

(R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol (cas: 851615-07-1) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Liquid chromatographic resolution of 1,1′-bi-2-naphthol and 3,3′-diaryl-1,1′-bi-2-naphthols on Pirkle-type chiral stationary phases based on leucine and phenylglycine was written by Hyun, Myung Ho;Kim, Kwang Soo;Cho, Yoon Jae. And the article was included in Journal of Liquid Chromatography & Related Technologies in 2005.Application In Synthesis of (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol The following contents are mentioned in the article:

Pirkle-type chiral stationary phases (CSPs) based on (S)-leucine and (S)-phenylglycine were applied in the resolution of 1,1′-bi-2-naphthol and 3,3′-diaryl-1,1′-bi-2-naphthols. Among the two Pirkle-type CSPs, the one based on (S)-N-(3,5-dinitrobenzoyl)leucine N-propylamide is excellent and most widely applicable. The elution orders for the resolution of 1,1′-bi-2-naphthol on the CSPs based on (S)-N-(3,5-dinitrobenzoyl)leucine N-propylamide and (S)-N-(3,5-dinitrobenzoyl)phenylglycine N-propylamide were opposite to those for the resolution of 3,3′-diaryl-1,1′-bi-2-naphthols. To rationalize the reversed elution orders, the authors proposed two different chiral recognition mechanisms based on the chromatog. resolution behaviors, with the aid of the CPK mol. model study. This study involved multiple reactions and reactants, such as (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol (cas: 851615-07-1Application In Synthesis of (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol).

(R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol (cas: 851615-07-1) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Application In Synthesis of (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

An enantioselective synthesis of 3,4-benzo-5-oxacephams was written by Koziol, Anna;Frelek, Jadwiga;Woznica, Magdalena;Furman, Bartlomiej;Chmielewski, Marek. And the article was included in European Journal of Organic Chemistry in 2009.COA of Formula: C40H26O2 The following contents are mentioned in the article:

The title compounds, e.g., I, represent an interesting group of 1-lactam antibiotics and active inhibitors of β-lactamase enzymes. All these compounds have one structural feature in common, an alkoxy fragment located at C4 of the azetidin-2-one ring. The most common strategy for the synthesis of 4-alkoxyazetidinones involves intramol. nucleophilic substitution at C4 that leads to ring closure. Such a displacement proceeds via the flat intermediate that supposedly has the structure of a mesomeric acyl ammonium cation. We herein report a novel and enantioselective chiral Lewis acid-mediated cyclization that affords the corresponding 5-oxacepham with excellent enantioselectivity and chem. yields of up to 50%. This may suggest that the high asym. induction is a result of a kinetic resolution of the initially formed racemic oxacepham. This study involved multiple reactions and reactants, such as (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol (cas: 851615-07-1COA of Formula: C40H26O2).

(R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol (cas: 851615-07-1) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.COA of Formula: C40H26O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Construction of Optically Active Quaternary Propargyl Amines by Highly Enantioselective Zinc/BINOL-Catalyzed Alkynylation of Ketoimines was written by Huang, Gaochao;Yin, Zengsheng;Zhang, Xingang. And the article was included in Chemistry – A European Journal in 2013.Application In Synthesis of (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol The following contents are mentioned in the article:

A general and efficient method for the highly enantioselective alkynylation of ketoimines through a zinc/1,1′-bi-2-naphthol (BINOL)-catalyzed process has been developed. A variety of ketoimines, including α-fluoroalkyl α-imine esters, α-aryl α-imine esters, and trifluoromethyl aryl ketoimines, are applicable and provide their corresponding quaternary propargyl amines in excellent yields with high ee values (up to 99 % ee). Both the steric and electronic effects of substituents at the 3,3′ positions of BINOL are critical for the reaction efficiency and enantioselectivity. To demonstrate the usefulness of the method, (R)-α-CF₃ α-proline has been prepared in a highly efficient manner. The notable features of this protocol are its broad substrate scope, high reaction efficiency (up to 99 %) and enantioselectivity (up to 99 % ee), low catalyst loading (5 mol % of BINOL derivative), and mild reaction conditions. This study involved multiple reactions and reactants, such as (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol (cas: 851615-07-1Application In Synthesis of (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol).

(R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol (cas: 851615-07-1) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Application In Synthesis of (R)-[1,3′:1′,1”:3”,1”’-Quaternaphthalene]-2′,2”-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts