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Synlett 2001; 2001(6): 0803-0805
DOI: 10.1055/s-2001-14606
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Palladium-Catalysed Synthesis of Enantiopure 1,2,4,5-Tetrahydro-1,4-benzodiazepin-3-(3H)-one Derivatives

Marta Catellani* , Claudio Catucci, Giuseppe Celentano, Rafaella Ferraccioli
  • *Dipartimento Di Chimica Organica e Industriale, Parco Area delle Scienze 17/A, I-43100 Parma, Italy; Fax + 39 (0)2 70 63 68 57; E-mail: rferra@icil64.cilea.it
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Publication Date:
31 December 2001 (online)

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A convenient procedure for the preparation of 1,2,4,5-tetrahydro-1,4-bezodiazepin-3-(3H)-one derivatives (S)-2 from chiral α-substituted N-n-butyl-N-(o-iodobenzyl)glycinamides (S)-1 has been developed. Seven-membered ring formation occurs through an intramolecular N-arylation catalysed by palladium and bis(phosphine) ligands. The use of chelating bis(phosphines) allows to minimize or entirely suppress carbon-2 racemisation which occurs when a mono(phosphine) ligand is used.

benzodiazepines - intramolecular N-arylations - palladium - bis(phosphine) ligands - chirality