"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. Cremonesi
Primo
;
P. Dalla Croce
Secondo
;
F. Fontana
Penultimo
;
C. La Rosa
Ultimo
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.
Settore CHIM/06 - Chimica Organica
2010
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/140534
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