Enantioselective Deprotonative Ring Contraction of N1-Methyl-N4-Boc-benzo[e][1,4]cliazepine-2,5-diones

N1-Methyl-N4-Boc-benzo[e][1,4] diazepine 2,5-diones were prepared in good yield an high stereo chemical purity from five amino acids Upon deprotonation these compounds undergo ring contraction to the corresponding quinolone 2,4-diones withhigh enantioselectivity, providing efficient entry to a potentially useful drug scaffold Mechanistic commentary and comparisons to related reactions are provided.