Juyeon Lee,Jihoon Lee,Ik Hwan Choi,Danila Ryzhikh,Ki Tae Kim,Minsoo Song,Gil Tae Hwang

Organic Letters

DOI: 10.1021/acs.orglett.6c02619

Abstract

We report the first direct solution-phase on-DNA Ugi three-component reaction for the selective synthesis of α-aminoamides under mild, DNA-compatible conditions. The optimized reaction provides selective access to the desired products by minimizing competing reaction pathways. The method exhibits broad substrate scope for DNA-conjugated anilines and is applicable to representative DNA-conjugated aldehydes and isocyanides. This work expands the repertoire of DNA-compatible multicomponent reactions and provides access to privileged α-aminoamide scaffolds for DNA-encoded libraries.