Intramolecular transamidation of β-lactams as a means for the enzymatic control of ring opening: Effect of substituents on the rate of reaction

Tetrahedron Letters

Volumn 39, Issue 51, 1998, Pages 9539-9542

  Banfi, Luca ^a   Guanti, Giuseppe ^a   Rasparini, Marcello ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

AMIDATION; ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032542169     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02118-2     Document Type: Article

References (23)

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14. 7. Other functional groups, for example the hydroxy group, were anticipated to be not nucleophilic enough, while the thiolate group was more problematic to study on a small scale because of its tendency to react with air to give disulfides.
15. 8. Side chains at position 4 were not included in this study for two reasons: a) stereoselective synthesis of trans lactendiynes disubstituted at position 4 of the β-lactam was expected to be problematic. b) The transition state for transamidation reaction would be in this case a bridged bicyclic ring instead than a ortho-fused byciclic ring and thus the reaction was foreseen to be more difficult.
16. 13C n.m.r. (in most cases), GC-MS (when feasible), and were all racemic.
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23. 15. Kindly gifted to us by Recordati (Unità Biochimici De.Bi).