An Efficient Asymmetric Synthesis of 2‐Substituted 1,4‐Benzodiazepin‐3‐one as a Potential Molecular Scaffold

Abstract

Abstract2‐Substituted 1,4‐benzodiazepine‐2‐one compounds (9–12) were obtained by a highly diastereoselective alkylation of a seven‐membered ring benzolactam (8) in the presence of (R)‐phenylglycinol as a chiral inductor. The corresponding acid derivative (16) afforded a conformationally constrained structure suitable for preparing peptidomimetic analogues useful as a novel molecular scaffold. After cleavage of the chiral appendage this approach might also lead efficiently to enantiomerically pure 2‐substituted benzodiazepines (15). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)