DOI: 10.1021/acs.orglett.6c04185 ISSN: 1523-7060
Photoredox/Cobalt-Catalyzed Stereoselective 2-Deoxyglycosylation of Glycals via MHAT-RPC with C/N/O-Nucleophiles
Qi Meng, Meitong Qu, Honglin Dong, Dongliang Zhang, Ge Zhang, Qian ZhangAbstract
Catalytic stereoselective synthesis of 2-deoxy-N-glycosides from stable, readily accessible glycosyl donors remains challenging, although these motifs are ubiquitous in bioactive molecules. We herein report an efficient and stereoselective radical approach for direct 2-deoxyglycosylation of glycals with simple Lewis basic anilines through a dual photoredox- and cobalt-catalyzed MHAT and nucleophilic amination process, enabling the synthesis of various β-N-glycosides in good to excellent yields. The method also applies to phenols, alcohols, and indoles with excellent stereoselectivity, providing a unique platform for stereoselective synthesis of valuable 2-deoxyglycosides and glycoside-based therapeutics.