Synthesis of cyclobutane serine analogues.
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-alpha-amino acid serine analogue (c(4)Ser); compounds 22 and 23. This synthesis covers a gap in knowledge in the broad field of restricted amino acids.
Avenoza
Alberto
A
Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, U.A.-C.S.I.C., E-26006 Logroño, Spain. alberto.avenoza@dq.unirioja.es
Busto
Jesús H
JH
Canal
Noelia
N
Peregrina
Jesús M
JM
D002384:Catalysis; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013816:Thermodynamics
D003503:Cyclobutanes; D007202:Indicators and Reagents; D012694:Serine