Asymmetric synthesis of all isomers of alfa-methyl-beta-phenylserine

  1. Avenoza, A. 1
  2. Cativiela, C. 2
  3. Corzana, F. 1
  4. Peregrina, J.M. 1
  5. 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

Zeitschrift:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Datum der Publikation: 2000

Ausgabe: 11

Nummer: 10

Seiten: 2195-2204

Art: Artikel

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DOI: 10.1016/S0957-4166(00)00149-X SCOPUS: 2-s2.0-0034595642 WoS: WOS:000087738400018 GOOGLE SCHOLAR

Andere Publikationen in: Tetrahedron: Asymmetry

Institutionelles Repository: lock_openOpen Access Editor

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Zusammenfassung

This report describes the synthesis of enantiomerically pure (2R,3R)-, (2R,3S)-, (2S,3S)- and (2S,3R)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoic acids, four quaternary α-amino acids, using a stereodivergent synthetic route and starting from (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals. The key step involves the asymmetric Grignard additions to the above chiral aldehydes, in which high levels of asymmetric induction are observed. Copyright (C) 2000 Elsevier Science Ltd.