Palladium-catalyzed stereoselective C-glycosylation of glycals with sodium arylsulfinates

• Main Authors: Ma, Jimei, Xiang, Shaohua, Jiang, Hong, Liu, Xue-Wei
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2015
• Subjects: DRNTU::Science::Chemistry::Organic chemistry
• Online Access: https://hdl.handle.net/10356/106693; http://hdl.handle.net/10220/25083; http://dx.doi.org/10.1002/ejoc.201403550
• Institution: Nanyang Technological University

An efficient glycosylation method to synthesize 2-deoxy-C-aryl glycosides was developed. This C-glycosylation strategy is based on a palladium-catalyzed desulfitative Ferrier-type coupling reaction of glycals and sodium arylsulfinates. A series of C-aryl glycosides were obtained in moderate to good yields with exclusive regio- and stereoselectivities. The anomeric selectivity was found to depend on the configuration of the C3 substituent of the glycals.