98777-16-3Relevant academic research and scientific papers
Regio- and Stereoselective Chan-Lam-Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines
Steemers, Luuk,Wijsman, Linda,van Maarseveen, Jan H.
supporting information, p. 4241 - 4245 (2018/10/02)
Efficient and scalable Cu(II)-mediated enol esterification methodology of carboxylic acids from alkenyl boroxines and boronic acids is presented. The reaction shows a wide scope in aliphatic and aromatic carboxylic acids in combination with several alkenyl boroxines. In the case of 2-substituted alkenyl boroxines the double bond configuration was fully retained in the enol ester product. Also N-hydroxyimides and imides could be transformed in the respective amidooxy vinyl enol ethers and vinyl enamides. Finally, with the exception of methionine, all other 19 canonical amino acids showed their compatibility to give the enol esters in a stereoselective fashion. (Figure presented.).
Titanium-mediated addition of grignard reagents to acyl cyanohydrins: Aminocyclopropane versus 1,4-diketone formation
Setzer, Paul,Forcher, Gwenael,Boeda, Fabien,Pearson-Long, Morwenna S. M.,Bertus, Philippe
supporting information, p. 171 - 180 (2014/01/06)
The 1,2-dianion reactivity of the reagent generated from EtMgBr and titanium isopropoxide was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples), giving both aminocyclopropane derivatives and 1,4-dicarbonyl compounds. When the reaction was performed in diethyl ether, 5-hydroxy-1,4-diketones were the main product. Under specific conditions (use of tetrahydrofuran and a bulky carboxylic moiety), the cyclopropane derivatives were obtained in good yields. The observed dichotomy may be explained by a ring-opening of the five-membered titanacycle intermediate followed by a nonselective acyl addition. The 1,2-dianion reactivity of the reagent generated from EtMgBr and Ti(OiPr)4 was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples). When the reaction was performed in diethyl ether, 1,4-diketones were mainly isolated. Under certain conditions, cyclopropane derivatives were also obtained in good yields. A mechanism rationalizing this dichotomy is presented. Copyright
A novel system for the synthesis of nitriles from carboxylic acids
Telvekar, Vikas N.,Rane, Rajesh A.
, p. 6051 - 6053 (2008/02/10)
A simple, mild and high yielding method for the conversion of various carboxylic acids to nitriles has been developed using diphosphorus tetraiodide in combination with ammonium carbonate at room temperature.
The effect of catechin derivatives on the enantioselectivity of lipase-catalyzed hydrolyses of alkynol benzoate esters
Nakamura, Kaoru,Takenaka, Keishi
, p. 415 - 422 (2007/10/03)
Polyphenols, such as (+)-catechin and pyrogallol could be used to enhance stereochemical control in the lipase-catalyzed hydrolysis of alkynol benzoate esters, leading to increased enantioselectivities in the kinetic resolution of alkynols with lipase Amano AH.
DABCO-Mediated Synthesis and Biological Activity of Cyanihydrin Esters
Hoffmann, H. M. R.,Ismail, Z. M.,Hollweg, Reiner,Zein, Abdul R.
, p. 1807 - 1810 (2007/10/02)
Cyanohydrin esters 1-31 have been prepared from α-ketonitriles and aldehydes using DABCO (1,4-diazabicyclooctane) as nucleophilic acylation catalyst.The modofied piperonal 8 was found to inhibit the formation of thromboxane synthetase.
Benzoxazinones et acyloxynitriles via des acyliminophosphorannes
Babin, Pierre,Clin, Bernard,Dunogues, Jacques
, p. 997 - 1000 (2007/10/02)
Ph3P=NSiMe3 reacts with acetyl and p-tolyl salicylic acid chlorides to afford the corresponding benzoxazinones: This new reaction allows the first preparation of the compound in which R1=Me, since the formation of the dimer, only provided by the unique route previously described, can be avoided.In contrast, o-acyl derivatives of lactic acid chlorides react with Ph3P=NSiMe3 to give the corresponding nitriles and not the expected oxazolones, as previously described.
