126771-32-2Relevant academic research and scientific papers
Dynamic Kinetic Resolution of Azlactones by a Chiral N, N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups
Mandai, Hiroki,Hongo, Kohei,Fujiwara, Takuma,Fujii, Kazuki,Mitsudo, Koichi,Suga, Seiji
supporting information, p. 4811 - 4814 (2018/08/24)
A dynamic kinetic resolution (DKR) of azlactones in the presence of benzoic acid and a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1i having two amide groups at the 3,3′-positions of a binaphthyl unit is developed. The reaction proceeded smoothly with a wide range of azlactones to provide α-amino acid derivatives with good to high enantiomeric ratios (er's). A multigram-scale reaction (2.5 g) for the DKR of azlactone 2d was also demonstrated, and the resulting product was converted to unnatural α-amino acid 6d′.
Br?nsted acid catalyzed azlactone ring opening by nucleophiles
Pereira, Adriane A.,De Castro, Pedro P.,De Mello, Amanda C.,Ferreira, Bruno R.V.,Eberlin, Marcos N.,Amarante, Giovanni W.
, p. 3271 - 3275 (2014/05/06)
Br?nsted acid catalyzed azlactone ring opening in the presence of different nucleophiles leading to the efficient synthesis of protected amides and amino esters is presented. Sixteen compounds were synthesized in good to excellent isolated yields. Mechani
Hydro-de-phosphoniation of 4-substituted-4-triphenylphosphonio-5(4H)-oxazolones with alcohols
Mazurkiewicz, Roman,Pierwocha, Anna W.,Brachaczek, Anna,Mitrus, Iwona
, p. 43 - 52 (2007/10/03)
4-Substituted-4-triphenylphosphonio-5(4H)-oxazolones with a bulky alkyl substituent at the position 4 treated with MeOH in the presence of DBU (1,8-diazobicyclo[5.4.0]undec-7-ene) at room temperature give corresponding N-acyl-α-amino acid esters. In the case of a smaller substituent at the position 4 (Me, MeOCH2), the triphenylphosphonium group was competitively displaced by the methoxy group. The latter reaction can be avoided by carrying out hydro-de-phosphoniation in CH2Cl2 in the presence of only 150% excess of i-PrOH at 50°C in the absence of DBU. Possible mechanisms of hydro-de-phosphoniation are discussed.
