2-Iodo-1-C-acceptor-substituted glycals: synthesis and transformation into 1,2-C,C-disubstituted glycals via Suzuki–Miyaura coupling reaction

Abstract

A series of 2-iodo-1-C-substituted glycals having electron withdrawing groups (CN, CO₂CH₃, CONH₂) at the C-1 carbon were synthesized from the parent 1-C-substituted glycals using N-iodosuccinimide or N-iodophtalimide and a Lewis acid. The utility of the iodoglycal derivatives has been demonstrated by Suzuki–Miyaura coupling reactions with aromatic and aliphatic boronic acids to give 1,2-C,C-disubstituted glycals in moderate to excellent yields.