727678-24-2Relevant academic research and scientific papers
Diastereoselectivity in the synthesis of unnatural α-amino acid esters by phase transfer catalysis
Tavares Lins, Francisco Furtado,Pereira Da Cunha, Lázaro,Memória Pouliquen, Yvone Brígido,Gomes Lemos, Telma Leda,De Mattos, Marcos Carlos
, p. 305 - 309 (2004)
Two unnatural α-amino acid esters were prepared in good yields via phase transfer catalyzed Michael addition of ethyl N-acetylaminocyanoacetate to chalcone and benzalketone. For both α-enones, a progressive increase in product diastereomeric excess (d.e.) was observed during the course of reaction, even in the absence of quaternary ammonium salt. However, for a fixed reaction time, higher d.e. values were obtained under phase transfer catalytic condition. Analogous reactions were performed using S-aryl thiocinnamates as Michael acceptors, affording a 2-pyrrolidinone in good yield but low d.e. These results were interpreted on the basis of the reversibility of the Michael reaction.
A novel approach to 1,2-dihydro-2-oxo-3-pyridinecarboxylic ester via aromatization induced by deamidation
Yu, Gang,Wang, Shaozhong,Wang, Kai,Hu, Yuefei,Hu, Hongwen
, p. 1021 - 1028 (2007/10/03)
A novel approach was developed for the preparation of 4,6-disubstituted-1, 2-dihydro-2-oxo-3-pyridinecarboxylic ester in moderate to good yields. This route involves a reaction sequence of Michael addition, transformation to ene-lactam, and aromatization, featuring easily available material, variable substituents, and good functional compatibility.
