Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors

  1. Pérez-Fernández, M. 1
  2. Avenoza, A. 1
  3. Busto, J.H. 1
  4. Peregrina, J.M. 1
  5. Rodríguez, F. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    GRID grid.119021.a

Journal:
ARKIVOC

ISSN: 1551-7004

Year of publication: 2010

Volume: 2010

Issue: 3

Pages: 191-202

Type: Article

Export: RIS

Metrics

Cited by

  • Scopus Cited by: 4 (12-06-2021)

Journal Citation Reports

  • Year 2010
  • Journal Impact Factor: 1.096
  • Best Quartile: Q3
  • Area: CHEMISTRY, ORGANIC Quartile: Q3 Rank in area: 34/56 (Ranking edition: SCIE)

SCImago Journal Rank

  • Year 2010
  • SJR Journal Impact: 0.411
  • Best Quartile: Q3
  • Area: Organic Chemistry Quartile: Q3 Rank in area: 106/174

Abstract

The synthesis of the 5-hydroxyproline derivatives 3a and 3b using cyclobutane serine analogs 1 and 2 as starting materials is reported. This process occurs with moderate cis/trans selectivity. A mechanism for this reaction is also proposed. Cyclobutane serine analog 1 was tested in tandem Michael and Wittig-like reactions, providing some evidence of the mechanism proposed.