308277-23-8Relevant academic research and scientific papers
Mechanochemical enzymatic resolution of N-benzylated-β3-amino esters
Pérez-Venegas, Mario,Reyes-Rangel, Gloria,Neri, Adrián,Escalante, Jaime,Juaristi, Eusebio
supporting information, p. 1728 - 1734 (2017/09/27)
The use of mechanochemistry to carry out enantioselective reactions has been explored in the last ten years with excellent results. Several chiral organocatalysts and even enzymes have proved to be resistant to milling conditions, which allows for rather efficient enantioselective transformations under ball-milling conditions. The present article reports the first example of a liquid-assisted grinding (LAG) mechanochemical enzymatic resolution of racemic β3-amino esters employing Candida antarctica lipase B (CALB) to afford highly valuable enantioenriched N-benzylated-β3-amino acids in good yields. Furthermore the present protocol is readily scalable.
Efficient resolution of racemic N-benzyl β3-amino acids by iterative liquid-liquid extraction with a chiral (salen)cobalt(iii) complex as enantioselective selector
Dzygiel, Pawel,Monti, Chiara,Piarulli, Umberto,Gennari, Cesare
, p. 3464 - 3471 (2008/09/20)
The efficient (up to 93% ee) resolution of racemic N-benzyl β3-amino acids has been achieved by an iterative (two cycle) liquid-liquid extraction process using a lipophilic chiral (salen)cobalt(iii) complex [CoIII(1)(OAc)]. As a result of the resolution by extraction, one enantiomer of the N-benzyl β3-amino acid predominated in the aqueous phase, while the other enantiomer was driven into the organic phase by complexation to cobalt. The complexed amino acid was then quantitatively released into an aqueous phase, by a reductive (CoIII → Co II) counter-extraction using l-ascorbic acid. The reductive cleavage allowed for the recovery of the cobalt(ii) selector in up to 90% yield (easily re-oxidable to CoIII with air/AcOH). The Royal Society of Chemistry.
N-benzylhydroxylamine addition to β-aryl enoates. Enantioselective synthesis of β-aryl-β-amino acid precursors
Sibi, Mukund P.,Liu, Mei
, p. 3393 - 3396 (2007/10/03)
(matrix presented) Chiral Lewis acid catalyzed N-benzylhydroxylamine addition to pyrrolidinone-derived enoates afforded β-aryl-β-amino acid derivatives in high enantiomeric purity with moderate to very good chemical efficiency.
