Selective Transformation of Norbornadiene into Functionalized Azaheterocycles and β-Amino Esters with Stereo- and Regiocontrol

Semghouli, Anas and Benke, Zsanett and Remete, Attila Márió and Novák, Tamás and Fustero, Santos and Kiss, Loránd (2021) Selective Transformation of Norbornadiene into Functionalized Azaheterocycles and β-Amino Esters with Stereo- and Regiocontrol. Chemistry an Asian Journal, 16 (23). pp. 3873-3881. ISSN 1861-471X

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Abstract

Abstract: Novel functionalized azaheterocycles with multiple chiral centers have been accessed from readily available norbornene β-amino acids or β-lactams across a stereocontrolled synthetic route, based on ring-opening metathesis (ROM) of the staring unsaturated bicyclic amino esters, followed by selective cyclization through ring-closing metathesis (RCM). The RCM transformations have been studied under various experimental conditions to assess the scope of conversion, catalyst, yield, and substrate influence. The structure of the starting norbornene β-amino acids predetermined the structure of the new azaheterocycles, and the developed synthetic route took place with the conservation of the configuration of the chiral centers.

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