A study on the induction of stereoselectivity in the Strecker synthesis of basic amino acid-derived α-amino nitriles
| Autor: | Rosario Herranz, M. Teresa García-López, Pilar Ventosa-Andrés |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
chemistry.chemical_classification
Stereochemistry Cyanide Organic Chemistry Strecker amino acid synthesis Absolute configuration Amino nitriles Catalysis Stereocenter Amino acid Inorganic Chemistry chemistry.chemical_compound chemistry Organic chemistry Stereoselectivity Physical and Theoretical Chemistry Selectivity |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2012.07.009 |
| Popis: | Diverse 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. This work was supported by the Spanish Ministerio de Ciencia e Innovación grant SAF2009-09323. P. V.-A. held a FPI fellowship from the Ministerio de Ciencia e Innovación. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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