Ji Young Ryu ,  Dohui Ku ,  Hayeong Shin ,  Yoojin Park ,  Hokyung Kim ,  Jihoon Lee ,  Gil Tae Hwang ,  Minsoo Song ,  Ki Tae Kim

Organic Letters

DOI: 10.1021/acs.orglett.5c04328

Abstract

The development of new on-DNA synthetic methods is crucial for efficient drug discovery using DNA-encoded libraries (DELs). Herein, we present a novel on-DNA approach based on hydrosulfonation of alkynylcarbonyl compounds to access β-sulfonyl-α,β-unsaturated carbonyl scaffolds bearing vinyl and γ-carbonyl sulfone skeletons. The reaction proceeds via a simple mix of alkynylcarbonyl compound and sodium sulfinate at 80 °C, showing moderate to good conversions, Z-geometry preference, and good DNA compatibility, supporting its utility in DEL construction.