Synthesis of a new enantiomerically pure constrained homoserine

  1. Avenoza, A. 1
  2. Cativiela, C. 2
  3. Fernández-Recio, M.A. 1
  4. Peregrina, J.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

Journal:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Year of publication: 1996

Volume: 7

Issue: 3

Pages: 721-728

Type: Article

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DOI: 10.1016/0957-4166(96)00067-5 SCOPUS: 2-s2.0-0029867765 WoS: WOS:A1996UD02000023 GOOGLE SCHOLAR

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Abstract

The use of the Diels-Alder reaction between 1,3-butadiene and chiral 2-acetamidoacrylates as the key step followed by stereocontrolled transformations allows the synthesis of (1S,3R)-1-amino-3-hydroxycyclohexanecarboxylic acid, a new type of constrained homoserine, with an excellent overall yield.