Synthesis and synthetic applications of 3-amino-Δ5-piperidein-2-ones: Synthesis of methionine-derived pseudopeptides

Tetrahedron

Volumn 55, Issue 33, 1999, Pages 10173-10186

  Estiarte, M Angels ^a   De Souza, Marcus V N ^a,b   Del Rio, Xavier ^a   Dodd, Robert H ^b   Rubiralta, Mario ^a   Diez, Anna ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b CNRS   (France)

Author keywords

Enamides; Lactams; Peptide mimetics; Piperideinones

Indexed keywords

LACTAM; METHIONINE DERIVATIVE; PIPERIDINE DERIVATIVE; PSEUDOPEPTIDE;

AMINATION; ARTICLE; CYCLIZATION; DIASTEREOISOMER; EXTRACTION; METHYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033551817     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00545-1     Document Type: Article

References (27)

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25. On one occasion enamides 19 (16%) were obtained together with oxazolidones 22 (29 %) and 23 (12 %), resulting from the loss of the tert-butyl protecting groups in the acid medium and cyclisation with the intermediate acyliminium salt. This explains the moderate yield of the reaction. In the absence of p-TsOH the reaction did not improve. (equation presented)
26. The absolute stereochemistry of the 3-position has not been determined. However, for the sake of clarity, we have called isomers a and b 3S* and isomers c and d 3R*.
27. 4 whose stereochemistry has now been confirmed by X-ray crystallography.