97485-16-0Relevant academic research and scientific papers
Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives
Wang, Tianli,Yu, Zhaoyuan,Hoon, Ding Long,Phee, Claire Yan,Lan, Yu,Lu, Yixin
supporting information, p. 265 - 271 (2016/01/25)
Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.
AN EFFICIENT TRANSFORMATION OF N-ACYL-α-AMINO ACIDS INTO DIACYLAMINES VIA 2,4-DISUBSTITUTED OXAZOL-5(4H)-ONES
Suda, Kohji,Hino, Fumio,Yijima, Chino
, p. 882 - 885 (2007/10/02)
Base-catalyzed oxygenative decarboxylation of a variety of 2,4-disubstituted oxazol-5(4H)-ones in benzene with triethylamine or in dimethylsulfoxide with potassium tert-butoxide gives diacylamines.KEYWORDS - base-catalyzed autooxidation; selective oxygenation; decarboxylation; oxazol-5(4H)-one; N-acyl-α-amino acid; diacylamine
