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Enantiodivergent Transannular Rearrangement of 3‐Isopropyl‐1,4‐benzodiazepine‐2,5‐dione by Memory of Chirality
Author(s) -
Farran Daniel,
Archirel Pierre,
Toupet Loïc,
Martinez Jean,
Dewynter Georges
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100030
Subject(s) - isopropyl , enantiomer , chemistry , chirality (physics) , stereochemistry , benzodiazepine , reactivity (psychology) , cope rearrangement , contraction (grammar) , medicinal chemistry , philosophy , physics , medicine , biochemistry , chiral symmetry breaking , receptor , alternative medicine , pathology , quantum mechanics , nambu–jona lasinio model , quark , linguistics
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.