Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions

• DOI: 10.1021/acs.orglett.0c00078
• Publication Date: 2020-02-06T12:44:50Z
• Authors: Peng Wen; Christopher J. Si...; Zhi-xiong Ma; Stephanie A. Blas...; Paul G. Balzer; Wenjing Ye; Xiyan Duan; Hao-Yuan Wang; Dan Yin; Christopher M. St...; Weiping Tang
• Keywords: Picolinic acid

A general method has been developed for the formation of glycosyl chlorides and bromides from picolinic esters under mild neutral conditions. Benchtop stable are activated by a copper(II) halide species to afford corresponding products in high yields with traceless leaving group. Rare β accessible via this route through neighboring group participation. Additionally, labile protecting groups previously not easily can be prepared.