"Chemical Equation Presented" The "Staudinger ketene-imine reaction" between ketenes generated from natural O,N-protected trans-4-hydroxy-L-prolines and the N-benzyl-N-benzylideneamine led to mixtures of diastereoisomeric, enantiomerically pure pyrrolidine-derived spiro-β-lactams with a relative cis configuration. These were transformed into the corresponding pyrroline-spiro-/β-lactams by means of treatment with a base and the new C=C double bond was submitted to a number of different reactions in order to evaluate its reactivity and obtain new polyheterocyclic enantiomerically pure spiro-β-lactams.
Enantiomerically pure polyheterocyclic spiro-beta-lactams from trans-4-hydroxy-L-proline / G. Cremonesi, P. Dalla Croce, F. Fontana, C. La Rosa. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 75:6(2010), pp. 2010-2017. [10.1021/jo100061s]
Enantiomerically pure polyheterocyclic spiro-beta-lactams from trans-4-hydroxy-L-proline
G. CremonesiPrimo
;P. Dalla CroceSecondo
;F. FontanaPenultimo
;C. La RosaUltimo
2010
Abstract
"Chemical Equation Presented" The "Staudinger ketene-imine reaction" between ketenes generated from natural O,N-protected trans-4-hydroxy-L-prolines and the N-benzyl-N-benzylideneamine led to mixtures of diastereoisomeric, enantiomerically pure pyrrolidine-derived spiro-β-lactams with a relative cis configuration. These were transformed into the corresponding pyrroline-spiro-/β-lactams by means of treatment with a base and the new C=C double bond was submitted to a number of different reactions in order to evaluate its reactivity and obtain new polyheterocyclic enantiomerically pure spiro-β-lactams.
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