A study on the induction of stereoselectivity in the Strecker synthesis of basic amino acid-derived alpha-amino nitriles

作者:Ventosa Andres Pilar; Teresa Garcia Lopez M; Herranz Rosario*
来源:Tetrahedron: Asymmetry , 2012, 23(15-16): 1198-1205.
DOI:10.1016/j.tetasy.2012.07.009

摘要

Diverse basic amino acid-derived alpha-amino nitriles have been synthesized via a modified Strecker reaction, using TMSCN as the cyanide source. It has been found that this synthesis is a slow thermodynamically controlled reaction, where it was difficult to induce stereocontrol. Moderate selectivity was induced by thermodynamic control of the reaction in MeOH. The absolute configuration at the stereogenic center generated was assigned by chemical correlation with 2-oxopiperazine derivatives.

  • 出版日期2012-8-31