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ChemInform Abstract The selective synthesis of the secondary amines (V) is achieved either with isolation of the Boc-derivatives (III) (→ (Va)) or in a one-pot procedure (→ (Vb)) starting from (I).
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-beta-lactams with a relative cis configuration. These were transformed into the corresponding pyrroline-spiro-beta-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-beta-lactams.
Nitrile imines react with 1‐phenylsulphonyl‐2‐benzoyl (or methoxycarbonyl)alkenes to give 4‐phenylsulphonyl‐5‐benzoyl (or methoxycarbonyl) substituted pyrazolines. The cycloaddition regioselectivity is discussed in terms of Frontier Orbital energies and coefficients.
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