10501-31-2Relevant academic research and scientific papers
Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters
Greenhalgh, Mark D.,Laina-Martín, Víctor,Neyyappadath, Rifahath M.,Qu, Shen,Smith, Andrew D.,Smith, Samuel M.
supporting information, p. 16572 - 16578 (2020/09/09)
A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.
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.
PYROLYSIS OF 2-ACETOXYCARBOXYLIC ACIDS
Galoci, Jan,Prochazka, Milos,Klinotova, Eva
, p. 1729 - 1733 (2007/10/02)
The pyrolysis of 2-acetoxycarboxylic acids may be described by the competing reactions R(1)R(2)C(OCOCH3)COOH -> (a) R(1)R(2)CO + CH3COOH + CO; (b) R(1)R(2)CO + CH3CHO + CO2, (c) CH3COOH + unsaturated acid.The transformation of a carbonyl compound is the general character of the pyrolysis of this group of substances.
