Enantiodivergent Transannular Rearrangement of 3-Isopropyl-1,4-benzodiazepine-2,5-dione by Memory of Chirality - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2011

Enantiodivergent Transannular Rearrangement of 3-Isopropyl-1,4-benzodiazepine-2,5-dione by Memory of Chirality

Résumé

An unprecedented reactivity has been introduced to 3-isopropyl-1,4-benzodiazepine-2,5-dione thanks to N-Boc activation. Under basic conditions, a transannular rearrangement occurred by ring contraction to furnish a 3-aminoquinoline-2,4-dione with good to excellent enantiomeric purity. Depending on the nature of the base, either enantiomer can be obtained in a stereocontrolled manner. This enantiodivergent synthesis could be assigned to the conformational equilibrium of the starting material, which was studied with the help of DFT calculations.

Dates et versions

hal-00602467 , version 1 (22-06-2011)

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Citer

Daniel Farran, Pierre Archirel, Loic Toupet, Jean Martinez, Georges Dewynter. Enantiodivergent Transannular Rearrangement of 3-Isopropyl-1,4-benzodiazepine-2,5-dione by Memory of Chirality. European Journal of Organic Chemistry, 2011, 2011 (11), pp.2043-2047. ⟨10.1002/ejoc.201100030⟩. ⟨hal-00602467⟩
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