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...

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Autores: Aydillo, C. [0000-0002-0542-967X], Jiménez-Osés, G. [0000-0003-0105-4337], Busto, J.H. [0000-0003-4403-4790], Peregrina, J.M. [0000-0003-3778-7065], Zurbano, M.M. [0000-0001-6370-3537], Avenoza, A. [0000-0002-5465-3555]
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2007
País:España
Recursos:Universidad de La Rioja (UR)
Repositorio:RIUR. Repositorio Institucional de la Universidad de La Rioja
OAI Identifier:oai:portal.dialnet.es:doc/5bbc6912b750603269e814a0
Acesso em linha:https://investigacion.unirioja.es/documentos/5bbc6912b750603269e814a0
Access Level:acceso abierto
Palavra-chave:Ab initio calculations
Alkylation
Amino acids
Asymmetric synthesis
Carbanions
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spelling Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective AlkylationsAydillo, C. [0000-0002-0542-967X]Jiménez-Osés, G. [0000-0003-0105-4337]Busto, J.H. [0000-0003-4403-4790]Peregrina, J.M. [0000-0003-3778-7065]Zurbano, M.M. [0000-0001-6370-3537]Avenoza, A. [0000-0002-5465-3555]Ab initio calculationsAlkylationAmino acidsAsymmetric synthesisCarbanionsA 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.2007info:eu-repo/semantics/articleSubtype: Articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://investigacion.unirioja.es/documentos/5bbc6912b750603269e814a0reponame:RIUR. Repositorio Institucional de la Universidad de La Riojainstname:Universidad de La Rioja (UR)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1002/CHEM.200601746info:eu-repo/semantics/altIdentifier/wos/WOS:000247219900016info:eu-repo/semantics/altIdentifier/pmid/17366514info:eu-repo/semantics/altIdentifier/pissn/0947-6539Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective Alkylations, 2007, vol. 13, núm. 17, pág. 4840-4848info:eu-repo/semantics/openAccessoai:portal.dialnet.es:doc/5bbc6912b750603269e814a02026-06-14T12:47:17Z
dc.title.none.fl_str_mv Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective Alkylations
title Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective Alkylations
spellingShingle Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective Alkylations
Aydillo, C. [0000-0002-0542-967X]
Ab initio calculations
Alkylation
Amino acids
Asymmetric synthesis
Carbanions
title_short Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective Alkylations
title_full Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective Alkylations
title_fullStr Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective Alkylations
title_full_unstemmed Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective Alkylations
title_sort Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective Alkylations
dc.creator.none.fl_str_mv Aydillo, C. [0000-0002-0542-967X]
Jiménez-Osés, G. [0000-0003-0105-4337]
Busto, J.H. [0000-0003-4403-4790]
Peregrina, J.M. [0000-0003-3778-7065]
Zurbano, M.M. [0000-0001-6370-3537]
Avenoza, A. [0000-0002-5465-3555]
author Aydillo, C. [0000-0002-0542-967X]
author_facet Aydillo, C. [0000-0002-0542-967X]
Jiménez-Osés, G. [0000-0003-0105-4337]
Busto, J.H. [0000-0003-4403-4790]
Peregrina, J.M. [0000-0003-3778-7065]
Zurbano, M.M. [0000-0001-6370-3537]
Avenoza, A. [0000-0002-5465-3555]
author_role author
author2 Jiménez-Osés, G. [0000-0003-0105-4337]
Busto, J.H. [0000-0003-4403-4790]
Peregrina, J.M. [0000-0003-3778-7065]
Zurbano, M.M. [0000-0001-6370-3537]
Avenoza, A. [0000-0002-5465-3555]
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Ab initio calculations
Alkylation
Amino acids
Asymmetric synthesis
Carbanions
topic Ab initio calculations
Alkylation
Amino acids
Asymmetric synthesis
Carbanions
description 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.
publishDate 2007
dc.date.none.fl_str_mv 2007
dc.type.none.fl_str_mv info:eu-repo/semantics/article
Subtype: Article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://investigacion.unirioja.es/documentos/5bbc6912b750603269e814a0
url https://investigacion.unirioja.es/documentos/5bbc6912b750603269e814a0
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/CHEM.200601746
info:eu-repo/semantics/altIdentifier/wos/WOS:000247219900016
info:eu-repo/semantics/altIdentifier/pmid/17366514
info:eu-repo/semantics/altIdentifier/pissn/0947-6539
Theoretical Evidence of Pyramidalized Bicyclic Serine Enolates in Highly Diastereoselective Alkylations, 2007, vol. 13, núm. 17, pág. 4840-4848
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:RIUR. Repositorio Institucional de la Universidad de La Rioja
instname:Universidad de La Rioja (UR)
instname_str Universidad de La Rioja (UR)
reponame_str RIUR. Repositorio Institucional de la Universidad de La Rioja
collection RIUR. Repositorio Institucional de la Universidad de La Rioja
repository.name.fl_str_mv
repository.mail.fl_str_mv
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