Abstract
AbstractAn 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.
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