1434254-02-0Relevant articles and documents
Chelation controlled reduction of N-protected β-amino ketones toward the synthesis of HPA-12 and analogues
Chacko, Shibin,Kalita, Mrinal,Ramapanicker, Ramesh
, p. 623 - 631 (2015/08/03)
Diastereoselective reduction of N-protected β-amino ketones does not proceed effectively under the conditions used for chelation controlled reductions of N-alkyl β-amino ketones. A thorough analysis of various conditions required for the stereoselective r
Synthesis of γ-oxo γ-aryl and γ-aryl α-amino acids from aromatic aldehydes and serine
Chacko, Shibin,Ramapanicker, Ramesh
, p. 7120 - 7128 (2013/02/21)
γ-Oxo α-amino acids and γ-aryl α-amino acids are compounds with very interesting biological properties and are active components of many drug molecules. Oxo amino acids are also used as synthetic precursors for a number of unnatural amino acids and amino alcohols. We report a very efficient synthesis of such compounds through the coupling of aromatic dithianes, prepared from aromatic aldehydes and an iodide derivative of serine. The dithiane groups in compounds thus obtained can be either hydrolyzed or reduced to generate 4-oxo-4-aryl or 4-aryl 2-amino butanol derivatives, respectively, which, on further transformations, can be converted into the title compounds. Starting with L-serine provides the corresponding D-amino acids with complete enantiopurity. The reported method is economically viable and complements the existing methods, which rely largely on cross-coupling reactions.
