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

AuthorsVentosa-Andrés, Pilar CSIC; García-López, M. Teresa CSIC; Herranz, Rosario CSIC ORCID
Issue Date2012
CitationTetrahedron Asymmetry 23: 1198-1205 (2012)
AbstractDiverse basic amino acid-derived α-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.
Identifiersdoi: 10.1016/j.tetasy.2012.07.009
issn: 0957-4166
e-issn: 1362-511X
Appears in Collections:(IQM) Artículos
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