Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective Alkylations
A new chiral serine equivalent and its enantiomer have been synthesized from (S)- and (R)-N-Bocserine methyl esters (Boc: tert-butyloxy-carbonyl). The use of these compounds as chiral building blocks has been demonstrated in the synthesis of α-alkyl α-amino acids by diastereoselective po tassium eno...
| Autores: | , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2007 |
| País: | España |
| Institución: | Universidad de La Rioja (UR) |
| Repositorio: | RIUR. Repositorio Institucional de la Universidad de La Rioja |
| OAI Identifier: | oai:portal.dialnet.es:doc/5bbc6912b750603269e814a0 |
| Acceso en línea: | https://investigacion.unirioja.es/documentos/5bbc6912b750603269e814a0 |
| Access Level: | acceso abierto |
| Palabra clave: | Ab initio calculations Alkylation Amino acids Asymmetric synthesis Carbanions |
| Sumario: | A new chiral serine equivalent and its enantiomer have been synthesized from (S)- and (R)-N-Bocserine methyl esters (Boc: tert-butyloxy-carbonyl). The use of these compounds as chiral building blocks has been demonstrated in the synthesis of α-alkyl α-amino acids by diastereoselective po tassium enolate alkylation reactions and subsequent acid hydrolyses. Theoretical studies were performed to eluci date the stereochemical outcome of both the formation of five-membered cyclic N,O-acetals and the subsequent alkylation process, which occurs with total retention of configuration. This feature could be explained in terms of the high degree of pyramidalization of enolate intermediates. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA. |
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