637337-12-3Relevant academic research and scientific papers
Enantioselective preparation of β2-amino acids with aspartate, glutamate, asparagine, and glutamine side chains
Lelais, Gerald,Campo, Marino A.,Kopp, Sascha,Seebach, Dieter
, p. 1545 - 1560 (2007/10/03)
(S)-β2-Homoamino acids with the side chains of Asp, Glu, Asn, and Gln have been prepared and suitably protected (N-Fmoc, CO 2′Bu CONHTrt) for solid-phase peptide syntheses. The key steps of the syntheses are: N-acylation of 5,5-diphe
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.
