7063-21-0Relevant academic research and scientific papers
Asymmetric Mannich synthesis of α-amino esters by anion-binding catalysis
Wasa, Masayuki,Liu, Richard Y.,Roche, Stéphane P.,Jacobsen, Eric N.
supporting information, p. 12872 - 12875 (2016/10/06)
We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is promoted by a chiral aminothiourea, which is proposed to operate cooperatively
Imidazolidene carboxylate bound MBPh4 complexes (M = Li, Na) and their relevance in transcarboxylation reactions
Van Ausdall, Bret R.,Poth, Nils F.,Kincaid, Virginia A.,Arif, Atta M.,Louie, Janis
experimental part, p. 8413 - 8420 (2011/12/16)
Combination of 1,3-bis(2,6-diisopropylphenyl)imidazolum-2-carboxylate (IPrCO2) with the Lewis acids MBPh4, where M = Li or Na, provided two separate complexes. The crystal structures of these complexes revealed that coordination to NaBPh4 yielded a dimeric species, yet coordination of IPrCO2 with LiBPh4 yielded a monomeric species. Combination of 1,3-bis(2,4,6-trimethylphenyl)imidazolum-2-carboxylate (IMesCO2) with LiBPh4 also afforded a dimeric species that was similar in global structure to that of the IPrCO2+NaBPh 4 dimer. In all three cases, the cation of the organic salt was coordinated to the oxyanion of the zwitterionic carboxylate. Thermogravimetric analysis of the crystals demonstrated that decarboxylation occurred at lower temperatures than the decarboxylation temperature of the parent NHC·CO2 (NHC = N-heterocyclic carbene). Kinetic analysis of the transcarboxylation of IPrCO2 to acetophenone with NaBPh 4 to yield sodium benzoylacetate was performed. First-order dependences were observed for IPrCO2 and acetophenone, whereas zero -order dependence was observed for NaBPh4. Direct dicarboxylation was observed when ItBuCO2 was added to MeCN in the absence of added MBPh4.
A PRODRUG COMPRISING BETA-KETO CARBOXYLIC ACID, BETA-KETO CARBOXYLIC ACID SALT OR BETA-KETO CARBOXYLIC ACID ESTER FOR DRUG DELIVERY
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Page/Page column 74, (2010/11/04)
There is provided a prodrug of a pharmaceutically active agent, said prodrug comprising a beta-keto carboxylic acid, a beta-keto carboxylic acid salt or a beta-keto carboxylic acid ester functional group, to a pharmaceutical composition comprising the prodrug, and to the use of the prodrug or composition for treatment of a mammalian subject suffering from a condition which can be cured or alleviated by administration of said pharmaceutically active agent. There is further provided a method of inhibiting decarboxylation of a compound comprising a beta-keto carboxylic acid or a salt thereof with a monovalent cation, characterized in that a dry salt of said beta-keto carboxylic acid with a divalent or polyvalent cation is prepared.
Utilisation of 1,3-dialkylimidazolium-2-carboxylates as CO 2-carriers in the presence of Na+ and K+: Application in the synthesis of carboxylates, monomethylcarbonate anions and halogen-free ionic liquids
Tommasi, Immacolata,Sorrentino, Fabiana
, p. 2141 - 2145 (2007/10/03)
1,3-Dialkylimidazolium-2-carboxylate compounds have recently been fully characterised. Here we describe the utilisation of 1,3-dimethyl (1a) and 1-butyl-3-methyl-imidazolium-2-carboxylate (1b) in a carboxylation reaction with transfer of the CO2 moiety to benzoylacetone and methanol for the synthesis, in high yield, of benzoylacetate and monoalkylcarbonate anions, respectively. Conversely, when compounds 1a and b are reacted with carbonylic substrates lacking C-H active bonds, a product resulting from nucleophilic attack of the 1,3-dialkylimidazol-2-ylidene species on the carbonyl moiety is obtained. The reported reactions can find applications in organic synthesis and in the synthesis of halogen-free ionic liquids.
