Stereoselective synthesis of (Z)-1, 3-bis(α, β-unsaturated carbonyl)-isoindolines from aldehydes and phenacyl azides under metal free conditions. Issue 75 (26th August 2021) - Prasad, Budaganaboyina
Abstract : We report herein our observation of an unprecedented stereoselective synthesis of 2 H -isoindolin-1, 3-ylidenes from 2-formylphenyl acrylates and phenacylazide in the presence of piperidine. Abstract : Here in the present manuscript, we report our observation of an unprecedented stereoselective synthesis of 2 H -isoindolin-1, 3-ylidenes from 2-(formylphenyl)acrylates and phenacylazide in the presence of piperidine. Unlike in our previous findings, in which we accessed 3-keto-isoquinolines from the same starting materials under slightly modified reaction conditions, this unexpected one-pot tandem reaction allows an efficient and simple method to access a variety of highly functionalized ethyl ( Z )-2-(( Z )-3-(2-oxo-2-arylethylidene)-2, 3-dihydro-1 H -benzo[ e ]isoindol-1-ylidene)-acetates in very good to excellent yields (up to 91%). The present methodology is compatible with a wide variety of functional groups.