261174-46-3Relevant academic research and scientific papers
Trans-hexahydrobenzoxazolidinones in the enantioselective synthesis of β2-amino acids containing proteinogenic side chains
Bandala, Yamir,Reyes-Rangel, Gloria,Obregon-Zuniga, Arturo,Cruz-Hernandez, Carlos,Corzo, Gerardo,Juaristi, Eusebio
, p. 2275 - 2283 (2014/04/17)
The use of enantiopure trans-hexahydrobenzoxazolidinones as chiral auxiliaries in the enantioselective synthesis of two β2-amino acids containing proteinogenic side chains (β2-hPhenylalanine and β2-hLysine), in both enantiomeric forms, is described. Absolute configurations were assigned on the basis of X-ray diffraction analysis and chemical correlation methods.
Benzyl N-[(benzyloxy)methyl]carbamate: An improved aminomethylation electrophile for the synthesis of (benzyloxy)carbonyl (Cbz)-protected chiral β2-amino acids
Brocklehurst, Cara E.,Furegati, Markus,Mueller-Hartwieg, J. Constanze D.,Ossola, Flavio,La Vecchia, Luigi
experimental part, p. 314 - 323 (2010/05/14)
α-Aminomethylation of (R)-DIOZ-alkylated (DIOZ=4-isopropyl-5,5- diphenyloxazolidin-2-one) substrates is a key step in the asymmetric synthesis of β2-amino acids, but it is unfortunately often accompanied by formation of transcarbamation by-prod
Enantioselective preparation of 2-aminomethyl carboxylic acid derivatives: Solving the β2-amino acid problem with the chiral auxiliary 4-isopropyl-5,5-diphenyloxazolidin-2-one (DIOZ)
Seebach, Dieter,Schaeffer, Laurent,Gessier, Francois,Bindschaedler, Pascal,Jaeger, Corinna,Josien, Delphine,Kopp, Sascha,Lelais, Gerald,Mahajan, Yogesh R.,Micuch, Peter,Sebesta, Radovan,Schweizer, Bernd W.
, p. 1852 - 1861 (2007/10/03)
Multigram amounts of suitably protected β2-amino acids with 17 of the 20 proteinogenic side chains are prepared by diastereoselective reactions of Li, B, or Ti enolates of the corresponding 3-acyl-4-isopropyl-5,5-diphenyloxazolidin-2-ones (acyl-DIOZ; 1) with appropriate electrophiles (amidomethylation, hydroxyalkylation, (benzyloxycarbonyl)methylation) in yields of 55-90% and with diastereoselectivities of 80 to > 97% (Scheme). The primary products 2-8 thus obtained are converted to protected β2-amino acids by standard procedures (Table 1). Many of the DIOZ derivatives are highly crystalline compounds (31 X-ray crystal structures in Table 2). The chiral auxiliary DIOZ, readily prepared in either enantiomeric form, is recovered with high yield.
