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Synthesis of Structurally Diverse Substituted Aziridinyl Glycoconjugates via Base-Mediated One-Pot Post-Ugi Cyclization.

Research paper by Rekha R Sangwan, Atul A Dubey, Gurudayal G Prajapati, Ravi Sankar RS Ampapathi, Pintu Kumar PK Mandal

Indexed on: 06 Apr '19Published on: 05 Apr '19Published in: Organic Letters



Abstract

The base-promoted intramolecular cyclization of Ugi-azide adduct has been demonstrated for the synthesis of highly substituted aziridinyl glycoconjugates in one pot. The reactions are scalable and efficient and have an operationally simple broad substrate scope. To gain insight into the mechanism of aziridine formation, DFT and control experiments show that the cyclization of the aziridine glycoconjugate pathway was preferred, as it proceeds with a low activation energy barrier (0.57 kcal mol), which supports our experimental observation.