Alpha-Alkylation vs. Retro-O-Michael / gamma-Alkylation of Bicyclic N,O-Acetals; an Entry to alpha-Methylthreonine

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

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

Revista:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Año de publicación: 2008

Volumen: 19

Número: 24

Páginas: 2829-2834

Tipo: Artículo

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DOI: 10.1016/J.TETASY.2008.11.031 SCOPUS: 2-s2.0-59349099003 WoS: WOS:000263642700012 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron: Asymmetry

Resumen

The synthesis of a new threonine equivalent based on a bicyclic N,O-acetal substructure incorporating four stereogenic centres is developed from Boc-l-threonine methyl ester in one step. Its use as an excellent chiral building block was demonstrated in a new diastereoselective synthesis of α-methylthreonine by an α-alkylation reaction and in the synthesis of chiral α,β-dehydroamino acid derivatives, using the tandem retro-O-Michael/γ-alkylation reactions as key steps. © 2008 Elsevier Ltd. All rights reserved.