Role of the Countercation in Diastereoselective Alkylations of Pyramidalized Bicyclic Serine Enolates. An Easy Approach to alfa-Benzylserine

  1. Jiménez-Osés, G. 1
  2. Aydillo, C. 1
  3. Busto, J.H. 1
  4. Zurbano, M.M. 1
  5. Peregrina, J.M. 1
  6. Avenoza, A. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Journal of Organic Chemistry

ISSN: 0022-3263

Año de publicación: 2007

Volumen: 72

Número: 14

Páginas: 5399-5402

Tipo: Artículo

DOI: 10.1021/JO070656B PMID: 17555358 SCOPUS: 2-s2.0-34447334168 WoS: WOS:000247612200049 GOOGLE SCHOLAR

Otras publicaciones en: Journal of Organic Chemistry

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Resumen

(Chemical Equation Presented) The use of a chiral serine equivalent as an excellent chiral building block has been demonstrated in the synthesis of α-benzylserine through a diastereoselective lithium enolate alkylation reaction and subsequent acid hydrolysis. The role of a coordinating countercation (lithium) in the alkylation reaction has been investigated. Theoretical studies have been performed in order to elucidate the stereochemical outcome of the alkylation process, which occurs with total retention of configuration. © 2007 American Chemical Society.