Synthesis of cyclobutane serine analogues

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Canal, N. 1
  4. Peregrina, J.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Aldizkaria:
Journal of Organic Chemistry

ISSN: 0022-3263

Argitalpen urtea: 2005

Alea: 70

Zenbakia: 1

Orrialdeak: 330-333

Mota: Artikulua

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DOI: 10.1021/JO048943S PMID: 15624942 SCOPUS: 2-s2.0-11844273833 WoS: WOS:000226508600043 GOOGLE SCHOLAR

Beste argitalpen batzuk: Journal of Organic Chemistry

Gordailu instituzionala: lock_openSarbide irekia Editor

Garapen Iraunkorreko Helburuak

Laburpena

(Chemical Equation Presented). In this paper, we describe a thermal [2 + 2] cycloaddition involving 2-acylaminoacrylates as electron-poor acceptor alkenes, a reaction that involves a Michael-Dieckmann-type process. The reaction gives rise to a new substituted cyclobutane skeleton that can be transformed into amino acid derivatives. For example, a number of transformations were carried out to give the two pairs of stereoisomers of the 2-hydroxycyclobutane-α- amino acid serine analogue (c4Ser); compounds 22 and 23. This synthesis covers a gap in knowledge in the broad field of restricted amino acids.