25409-25-0Relevant academic research and scientific papers
Isopropenyl acetate: A cheap and general acylating agent of alcohols under metal-free conditions
Temperini, Andrea,Minuti, Lucio,Morini, Tommaso,Rosati, Ornelio,Piazzolla, Francesca
, p. 4051 - 4053 (2017/09/27)
Functionalized primary, secondary and tertiary alcohols are efficiently acetylated by isopropenyl acetate and catalytic p-TsOH.
Chemoenzymatic synthesis of both enantiomers of 3-hydroxy- and 3-amino-3-phenylpropanoic acid
Varga, Annamaria,Zaharia, Valentin,Nogradi, Mihaly,Poppe, Laszlo
, p. 1389 - 1394 (2013/12/04)
Ethyl (S)-3-hydroxy-3-phenylpropionate (S)-2 was obtained by the asymmetric reduction of ethyl 3-phenyl-3-oxopropionate 1 with the yeast Saccharomyces cerevisiae (ATCC 9080). The kinetic resolution of racemic ethyl 2-acetoxy-3-phenyl-propionate rac-3 with the same microorganism, gave after hydrolysis ethyl (R)- and (S)-3-hydroxy-3-phenylpropionates (R)-2 and (S)-2 which were converted by a straightforward series of reactions to the enantiomers of 3-amino-3-phenyl-propionic acids (S)-6 and (R)-6. The asymmetric reduction and hydrolytic kinetic resolution were also tested with several other whole cell systems under a variety of conditions.
Lipases A and B from Candida antarctica in the enantioselective acylation of ethyl 3-heteroaryl-3-hydroxypropanoates: Aspects on the preparation and enantiopreference
Brem, Juergen,Liljeblad, Arto,Paizs, Csaba,Tosa, Monica Ioana,Irimie, Florin-Dan,Kanerva, Liisa T.
, p. 315 - 322 (2011/05/19)
The preparative scale kinetic resolution of racemic ethyl 2- and 3-furyl- and 2- and 3-thienyl-3-hydroxypropanoates has been performed by Candida antarctica lipases A and B with vinyl esters. A study based on the present work together with the literature has been carried out in terms of lipase enantiopreference and substrate structure. We also discuss the excellent behavior of the lipase A in O-acylations of secondary alcohols with respect to enantiopreference.
Synthesis of Novel Diastereomeric Diphosphine Ligands and Their Applications in Asymmetric Hydrogenation Reactions
Qiu, Liqin,Qi, Jianying,Pai, Cheng-Chao,Chan, Shusun,Zhou, Zhongyuan,Choi, Michael C. K.,Chan, Albert S. C.
, p. 4599 - 4602 (2007/10/03)
(Matrix Presented) Diastereomeric biaryl diphosphine ligands 10 and 11 with added chiral centers on the backbone were synthesized. Substrate-directed asymmetric synthesis occurred in the coupling step of the preparation of the diastereomeric diphosphine oxides. The diastereomeric diphosphine oxides were easily separated by column chromatography with silica gel. Ruthenium catalysts containing these ligands were highly effective in the hydrogenation of 2-(6′-methoxy-2′-naphthyl)propenoic acid and β-ketoesters. The additional chiral centers had a significant influence on the enantioselectivity and activity of the catalysts.
Reduction of Arylcarbonyl Using Zinc Dust in Acetic Acid
Rani, B. Radha,Ubukata, Makoto,Osada, Hiroyuki
, p. 282 - 284 (2007/10/02)
Zinc dust in acetic acid has been found to be a versatile and chemoselective reagent for the reduction of various arylcarbonyls to the corresponding alcohols or their acetates in fair yields.
Regioselective Oxidative Cleavage of Functionalized Unsymmetric Tetraalkylstannanes via Ozone
Linderman, Russell J.,Jaber, Mohamed
, p. 5993 - 5996 (2007/10/02)
The direct oxidation of (α-alkoxyalkyl)trialkylstannanes to esters by reaction with ozone is described.
Cobalt(II) Chloride Catalyzed Acylation of Alcohols with Acetic Anhydride: Scope and Mechanism
Iqbal, Javed,Srivastava, Rajiv Ranjan
, p. 2001 - 2007 (2007/10/02)
Cobalt(II) chloride catalyzes the acetylation of a variety of alcohols with acetic anhydride in excellent yield.Primary hydroxyl groups can be selectively acylated in the presence of secondary and tertiary ones while the secondary hydroxyl groups can be preferentially acetylated in the presence of tertiary ones.Tertiary alcohols have been found to give ketones, acetoacetates, olefins, and diketene in addition to the acetate.The β-hydroxy esters and ketones can be acylated under these conditions without any elimination, and this reaction has been compared with 4-(dimethylamino)pyridine (DMAP)-mediated acylations where elimination of the resulting β-acetoxy carbonyl compound is observed.A detailed investigation of the acylation of tertiary alcohols has revealed that these reactions proceed via a tertiary alkoxy radical and ketene.A mechanism for these acylations is proposed by invoking an electron-transfer process.
Organomanganese (II) reagents XX1: Manganese mediated Barbier and Reformatsky like reactions. An efficient route to homoallylic alcohols and β-acetoxyesters
Cahiez,Chavant
, p. 7373 - 7376 (2007/10/02)
Allylic halides and α-bromoesters react with manganese metal in ethyl acetate; THF can also be used as solvent if a catalytic amount of zinc chloride is added to the reaction mixture. When the reaction is performed in the presence of various aldehydes or
STUDIES ON PIG LIVER ESTERASE-MEDIATED HYDROLYSES OF 3-HYDROXY ESTERS
Santaniello, Enzo,Ferraboschi, Patrizia,Grisenti, Paride,Manzocchi, Ada,Trave, Susanna
, p. 581 - 584 (2007/10/02)
At 25 deg C, the pig liver esterase (PLE)-catalyzed hydrolyses of 3-hydroxy esters 2 and 3 proceed in aqueous phosphate buffer with moderate enantioselectivity, which can be increased by carrying out the reaction in an aqueous medium containing 20percent
