Synthesis of α,β-diamino acid derivatives via asymmetric Mannich reactions of glycine imino esters catalyzed by a chiral phosphoramidite·silver complex
| Autor: | José M. Sansano, Carmen Nájera, Loane Serrano, Alberto Cayuelas |
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| Přispěvatelé: | Universidad de Alicante. Departamento de Química Orgánica, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica, Síntesis Asimétrica (SINTAS) |
| Rok vydání: | 2014 |
| Předmět: |
Acid derivatives
chemistry.chemical_classification Phosphoramidite Aldimine Silver Stereochemistry Organic Chemistry Enantioselective synthesis Diamino acid Catalysis Adduct Inorganic Chemistry chemistry.chemical_compound Química Orgánica Tosyl chemistry Glycine heterocyclic compounds Physical and Theoretical Chemistry |
| Zdroj: | RUA. Repositorio Institucional de la Universidad de Alicante Universidad de Alicante (UA) |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2014.11.009 |
| Popis: | AgOTf·phosphoramidite complexes efficiently catalyze the enantioselective Mannich-type reaction between benzophenone-imine glycine methyl ester and N-tosyl aldimines in the absence of a base. The corresponding syn-adducts, which are the direct precursors of α,β-diamino acids, are obtained with moderate to good syn-diastereoselectivities (up to 9:1) and high enantioselectivities (up to 99% ee). This work has been supported by the Spanish Ministerio de Ciencia e Innovación (MICINN) (Consolider INGENIO 2010 CSD2007-00006, CTQ2010-20387, CTQ2013-43446-P), FEDER, Generalitat Valenciana (PROMETEO/2009/039, and PROMETEOII 2014/017), and by the University of Alicante. L. S. thanks University of Edinburgh for an ERASMUS fellowship. |
| Databáze: | OpenAIRE |
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