Preparation and synthetic applications of (S)- and (R)-N-Boc-N,O-isopropylidene-alfa-methylserinals: asymmetric synthesis of (S)- and (R)-2-amino-2-methylbutanoic acids (Iva)

  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 Universidad de Zaragoza
    info

    Universidad de Zaragoza

    Zaragoza, España

    ROR https://ror.org/012a91z28

Zeitschrift:
Journal of Organic Chemistry

ISSN: 0022-3263

Datum der Publikation: 1999

Ausgabe: 64

Nummer: 22

Seiten: 8220-8225

Art: Artikel

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DOI: 10.1021/JO990957O SCOPUS: 2-s2.0-0033615484 WoS: WOS:000083520300025 GOOGLE SCHOLAR

Andere Publikationen in: Journal of Organic Chemistry

Institutionelles Repository: lock_openOpen Access Editor

Zusammenfassung

This report describes an efficient and convenient large-scale synthesis procedure for (S)- and (R)-N-Boc-α-methylserinal acetonides (3 and 4) starting from (R)-2-methylglycidol 5. The application of both of these compounds as valuable chiral building blocks in the asymmetric synthesis of α-methylamino acids is also demonstrated by the synthesis of (S)- and (R)- isovalines (Iva) (6 and 7).