29071-09-8Relevant articles and documents
Controlled meta-Selective C-H Mono- And Di-Olefination of Mandelic Acid Derivatives
Muthuraja, Perumal,Usman, Rahamdil,Sajeev, Revathy,Gopinath, Purushothaman
supporting information, p. 6014 - 6018 (2021/08/03)
Mandelic acids represent a key structural motif present in many drug molecules. Herein, we report the controlled meta-selective mono- and diolefination of mandelic acids by the careful design of the substrate and oxidant. Furthermore, free meta-functional
An efficient enzymatic aminolysis for kinetic resolution of aromatic α-hydroxyl acid in non-aqueous media
Chen, Shan,Liu, Fuyan,Zhang, Kuan,Huang, Hansheng,Wang, Huani,Zhou, Jiaying,Zhang, Jing,Gong, Yiwei,Zhang, Dela,Chen, Yiping,Lin, Chang,Wang, Bo
supporting information, p. 5312 - 5314 (2016/11/16)
A new and highly efficient enzymatic aminolysis approach for kinetic resolution of aromatic α-hydroxy acid in non-aqueous media has been developed. The corresponding α-hydroxyl acid ester was employed as the substrate, and commercially available Candida antarctica lipase B is used as the biocatalyst, anhydrous ammonia is the resolving agent. Reactions can be proceeded smoothly in organic solvent at ambient temperatures. High concentration of substrate is allowed due to the application of organic media and the products are obtained in yields of up to 49% with ee values of up to 99%, and with E value of >300, representing an appealing and promising protocol for large-scale preparations.
Silica sulfuric acid as a highly efficient catalyst for the synthesis of diarylacetic acids
Moore, Desiree L.,Denton, Allison E.,Kohinke, Rose M.,Craig, Brandon R.,Brenzovich, William E.
, p. 604 - 612 (2016/07/06)
ABSTRACT: An efficient heterogeneous method for the synthesis of diarylacetic acids was developed utilizing silica sulfuric acid as a catalyst. The reaction is highly efficient with a small amount of catalyst for the combination of a variety of electron-n
Α-hydroxyacid salt
-
, (2018/02/14)
PROBLEM TO BE SOLVED: To provide a novel method for manufacturing a salt of α-hydroxy acid as an intermediate for synthesizing α-hydroxy acid derivatives which promotes carboxylation promptly by the COsupplementation reaction even if the substrate having
Carboxylation with CO2 via brook rearrangement: Preparation of α-hydroxy acid derivatives
Mita, Tsuyoshi,Higuchi, Yuki,Sato, Yoshihiro
supporting information, p. 14 - 17 (2014/01/23)
In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO 2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.
Synthesis of arylglycine and mandelic acid derivatives through carboxylations of α-amido and α-acetoxy stannanes with carbon dioxide
Mita, Tsuyoshi,Sugawara, Masumi,Hasegawa, Hiroyuki,Sato, Yoshihiro
experimental part, p. 2159 - 2168 (2012/06/01)
Incorporation reactions of carbon dioxide (CO2) with N-Boc-α-amido and α-acetoxy stannanes were developed using CsF as a mild tin activator. Monoprotected α-amido stannanes could be used, and the corresponding arylglycine derivatives were obtained in moderate-to-high yields under 1 MPa (10 atm) of CO2 pressure. α-Acetoxy stannanes also underwent carboxylation to afford mandelic acid derivatives in excellent yields under ambient CO2 pressure. Both transformations enabled the synthesis of α-tertiary and α-quaternary carboxylic acid derivatives. In addition, the chirality of (S)-N-tert-butylsulfonyl-α- amido stannanes was transferred with up to 90% inversion of configuration at 100 °C.
A practical and inexpensive 'convertible' isonitrile for use in multicomponent reactions
Le, Hoang V.,Fan, Lijun,Ganem, Bruce
supporting information; experimental part, p. 2209 - 2211 (2011/05/09)
N-tert-Butylamides are readily converted into the corresponding carboxylic acids by simple nitrosation. The process, which occurs under mild nonaqueous conditions, leaves carboxylic esters untouched and transforms multicomponent reaction products into useful building blocks for further synthetic elaboration.
Design and structure-activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): Tetramic, tetronic acids and dihydropyridin-2-ones
Peukert, Stefan,Sun, Yingchuan,Zhang, Rui,Hurley, Brian,Sabio, Mike,Shen, Xiaoyu,Gray, Christen,Dzink-Fox, JoAnn,Tao, Jianshi,Cebula, Regina,Wattanasin, Sompong
, p. 1840 - 1844 (2008/09/19)
Based on a pharmacophore hypothesis substituted tetramic and tetronic acid 3-carboxamides as well as dihydropyridin-2-one-3-carboxamides were investigated as inhibitors of undecaprenyl pyrophosphate synthase (UPPS) for use as novel antimicrobial agents. S
Kinetic resolution of α-acetoxy N-acyl oxazolidinethiones by a chiral O-nucleophilic acyl transfer catalyst
Nolle, Gregory T.,Sammakia, Tarek,Steel, Peter J.
, p. 13502 - 13503 (2007/10/03)
The kinetic resolution of α-acetoxy N-acyl oxazolidinethiones using the chiral, nonracemic O-nucleophilic acyl transfer catalyst 8 is described. The reaction proceeds on a variety of substrates in excellent yields, with s-factors ranging from 17 to 31. Copyright
Hydrolysis of nitriles using an immobilized nitrilase: Applications to the synthesis of methionine hydroxy analogue derivatives
Rey, Patrick,Rossi, Jean-Christophe,Taillades, Jacques,Gros, Georges,Nore, Olivier
, p. 8155 - 8162 (2007/10/03)
Mild and selective hydrolysis of a large range of nitriles leading to carboxylic acids was achieved under neutral conditions by an immobilized and genetically modified enzyme preparation from Alcaligenes faecalis ATCC8750. This immobilized nitrilase has been shown to be an effective catalyst for the stereoselective hydrolysis of mandelonitrile 1a to R-(-)-mandelic acid 1c. This method is particularly useful for the production of hydroxy analogues of methionine derivatives 2c-4c that could have an interest in cattle feeding and for the transformation of compounds containing other acid- or base-sensitive groups 3a-10a. A series of aliphatic dinitriles 11a-15a was hydrolyzed to the corresponding cyano acids. The suitability of the immobilized catalyst as a robust and versatile biocatalyst is discussed, and models to account for the stereoselectivity of the enzymic hydrolysis have been proposed.
