1055324-92-9Relevant academic research and scientific papers
New approach to exclusive formation of both enantiomers of β-amino acid derivatives
Pinho e Melo, Teresa M.V.D.,Cardoso, Ana Lúcia,Palacios, Francisco,de los Santos, Jesús M.,Pais, Alberto A.C.C.,Abreu, Paulo E.,Paix?o, José A.,Beja, Ana Matos,Ramos Silva, Manuela
, p. 8141 - 8148 (2008/12/21)
A highly selective two-step approach to chiral β-amino esters via the hydride reductive amination of chiral allenes is reported. β-Enamino esters were obtained from the nucleophilic addition of amines to 2,3-allenoates bearing a chiral auxiliary. The reduction of the (1R)-(-)-10-phenylsulfonylisobornyl β-enamino esters gave the corresponding β-amino esters with S configuration whereas the reduction of the (1S)-(+)-10-phenylsulfonylisobornyl β-enamino esters led to β-amino esters with R configuration. The rationalization of the observed selectivity was supported by semi-empirical molecular orbital calculations (PM3).
