Chiral bronsted acid mediated glycosylation
WebDec 15, 2013 · It was subsequently found that a combination of Brønsted acid (carboxylic acid) and Lewis acid (MgBr2) was unique in catalyzing the desired glycosylation reaction. Thus, it was concluded that the two acids act synergistically to catalyze the … WebJun 14, 2024 · Based on their mechanistic studies, they proposed that chiral Brønsted acid catalyst 6 stimulated both the acceptor and the OTCA donor promoting an S N 2-type reaction with R -enantiomer of the racemic mixture of secondary alcohols to form a chiral transition state like 11, which accounts for the high 1,2- trans selectivity. SCHEME 3 …
Chiral bronsted acid mediated glycosylation
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WebJul 21, 2024 · Abstract Chiral Brønsted acids have found widespread applications as organocatalysts. Weakly acidic species such as diols and (thio)ureas, typically classified as hydrogen bonding catalysts, as well as … WebSep 23, 2013 · Chiral Brønsted acid mediated glycosylation with recognition of alcohol chirality. Kimura T 1, Sekine M, Takahashi D, Toshima K. Author information. Affiliations. 1 author. 1. ... Glycosylation catalyzed by a chiral Bronsted acid. Cox DJ, Smith MD, Fairbanks AJ. Org Lett, (7):1452-1455 2010 MED: 20249058 Show 10 more references …
WebMar 1, 2010 · In early 2010, the Fairbanks' group introduced a chiral BINOLderived phosphoric acid as chiral catalysts (R)-6 and (S)-6 for efficient 1,2-trans selective … WebNov 1, 2008 · Chiral Bronsted Acid: Innovations and Application to Regiodivergent Glycosylations Thesis Jan 2024 Tay Rosenthal View Show abstract Organocatalytic Enantioselective Friedel‐Crafts Alkylation...
WebThe use of a chiral Brønsted acid catalyst for the activation of trichloroacetimidate glycosyl donors has been demonstrated for the first time. In toluene the chirality of the acid … WebAbstract The use of a chiral Brønsted acid catalyst for the activation of trichloroacetimidate glycosyl donors influences the stereochemical outcome of glycosylation processes in toluene, hinting that perhaps diastereocontrol may become achievable through the judicious use of chiral organic catalysts. see article for more examples Key Words
WebChiral Brønsted acids are powerful organocatalysts for a great variety of asymmetric nucleophilic additions to imines (Scheme 1, eq. 1).1 In such reactions, the imine is protonated by the chiral Brønsted acid, with the resulting chiral anion directing the enan tiofacial differentiation upon attack of the nucleophile onto the iminium cation ...
WebKimura, Tomoya, et al. "Chiral Brønsted Acid Mediated Glycosylation With Recognition of Alcohol Chirality." Angewandte Chemie (International Ed. in English), vol. 52, no. 46, … devops tools salt stack under which typeWebApr 5, 2024 · Download Citation Brønsted-Acid-Catalyzed Friedel-Crafts Reaction and Electrocyclization Cascade of Indoles with α-Functionalized Carbonyls Reported here is an efficient Friedel-Crafts-type ... church indianapolisWebOct 13, 2014 · The stereochemical outcome of glycosylation reactions of 2-deoxy-sugar trichloroacetimidates promoted by chiral Brønsted acids is shown to be dependent on both the chirality of the catalyst... devops training and certification iantWebNov 11, 2013 · Chiral Brønsted acid mediated glycosylation with recognition of alcohol chirality Angew Chem Int Ed Engl. 2013 Nov 11;52(46):12131-4. doi: … church indianolaWebT Kimura, M Sekine, D Takahashi, K Toshima, Chiral Brønsted acid mediated glycosylation with recognition of alcohol chirality. Angew Chem Int Ed Engl 52, … church indianola iowaWebJan 19, 2024 · With the introduction of chiral BINOL-derived N-triflyl phosphoramides in 2006, asym. Bronsted acid catalysis is no longer restricted to reactive substrates. Also certain carbonyl compds. can be activated through these stronger Bronsted acid catalysts. In dealing with sensitive substrate classes, chiral dicarboxylic acids proved of particular ... devops training in gurgaonWebChiral Brønsted Acid Mediated Glycosylation with Recognition of Alcohol Chirality. †. Tomoya Kimura, Tomoya Kimura. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan) … church in didcot