173258-54-3Relevant academic research and scientific papers
Synthesis of Optically Active α,β-Disubstituted β-Amino Nitriles and β-Amino Acids Starting from Asparagine
Gmeiner, Peter,Hummel, Evi,Haubmann, Christian
, p. 1987 - 1992 (2007/10/03)
Starting from the enantiomerically pure building block 2 which is readily available from D-asparagine α,β-disubstituted β-amino nitriles and β-amino acids could be synthesized.After deprotonation of the nitrile α-position the introduction of substituents was performed by alkylation of either 2 or the TBDMS-protected derivative 3.Starting from the β-homoserine equivalent 2 the reaction proceeds via a dianionic intermediate resulting in a preferred formation of the threo-configurated products 6a,b (ratio of isomers: 7:1).Modification of the side chain was demonstrated by displacement reactions with LiBH4 or potassium thiacetate. - Keywords: β-Amino nitriles; β-Amino acids; Diastereoselective alkylation
