111170-56-0Relevant articles and documents
Towards sustainable kinetic resolution, a combination of bio-catalysis, flow chemistry and bio-based solvents
Iemhoff, Andree,Sherwood, James,McElroy, Con R.,Hunt, Andrew J.
, p. 136 - 140 (2018)
The esterification of 2-phenylpropionic acid was investigated as a model system for enzyme catalysed (CALB, Novozyme 435) reactions in bio-based solvents. A multi-parameter correlation taking into account solvent parameters was developed to explain experimental observations. A continuous flow process using p-cymene as the solvent was operated over several weeks, thus combining a sustainable solvent and flow chemistry for kinetic resolution.
Resolution of (RS)-2-phenylpropanoic acid by enantioselective esterification with dry microbial cells in organic solvent
Gandolfi, Raffaella,Gualandris, Roberto,Zanchi, Chiara,Molinari, Francesco
, p. 501 - 504 (2001)
The microbial direct esterification of racemic 2-phenyl-1-propanoic acid with ethanol by lyophilized mycelium of Aspergillus oryzae MIM and Rhizopus oryzae CBS 112.07 in organic solvents has been investigated. Dry cells of Rhizopus oryzae CBS 112.07 gave the (R)-ethyl ester with high enantiomeric excess (>97%) when the biotransformation was carried out in heptane or pentadecane. Dry mycelium of Aspergillus oryzae MIM furnished the ethyl ester of (S)-(+)-2-phenylpropanoic acid with 90% enantiomeric excess when used in toluene in a temperature range of 20-40°C.
Synthesis method of (S)-2-aryl propionate compound
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Paragraph 0096-0099; 0120-0123, (2020/08/09)
The invention discloses a synthesis method of a (S)-2-aryl propionate compound. The (S)-2-aryl propionate compound shown in the formula IV is obtained by taking a compound shown in a formula I and a compound shown in a formula II as raw materials and reacting under the conditions of a chiral ligand shown in a formula III, a nickel catalyst, a photocatalyst, a reducing agent and alkali under the condition of visible light. The method has the advantages of cheap and easily available raw materials, convenient generation, mild conditions, environmental protection and safety, the photocatalyst canbe recycled, the production cost is greatly reduced, the test operation is simple, less waste is generated, and the method can be developed into an industrial production method.
Iron-Catalyzed Enantioselective Cross-Coupling Reactions of α-Chloroesters with Aryl Grignard Reagents
Jin, Masayoshi,Adak, Laksmikanta,Nakamura, Masaharu
supporting information, p. 7128 - 7134 (2015/06/25)
The first iron-catalyzed enantioselective cross-coupling reaction between an organometallic compound and an organic electrophile is reported. Synthetically versatile racemic α-chloro- and α-bromoalkanoates were coupled with aryl Grignard reagents in the presence of catalytic amounts of an iron salt and a chiral bisphosphine ligand, giving the products in high yields with acceptable and synthetically useful enantioselectivities (er up to 91:9). The produced α-arylalkanoates were readily converted to the corresponding α-arylalkanoic acids with high optical enrichment (er up to >99:1) via simple deprotections/recrystallizations. The results of radical probe experiments are consistent with a mechanism that involves the formation of an alkyl radical intermediate, which undergoes subsequent enantioconvergent arylation in an intermolecular manner. The developed asymmetric coupling offers not only facile and practical access to various chiral α-arylalkanoic acid derivatives, which are of significant pharmaceutical importance, but also a basis of controlling enantioselectivity in an iron-catalyzed organometallic transformation. (Chemical Equation Presented).
