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A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

In our recently developed interrupted Pummerer reaction mediated (IPRm) glycosylation with S-2-[(propan-2-yl)sulfinyl] benzyl (SPSB) glycosides as glycosyl donors, the anomeric leaving groups were ...

Attachment of various 3-aminodeoxy sugars to natural products or drugs is a prominent method for new drug development. However, access to structurally diversified 3-aminodeoxy sugars and glycosylation with aglycons are challenging. We synthesized a variety of unnatural 3-aminodeoxy sugars via diversified functionalization of a common glycal intermediate bearing a cyclic sulfamidate ketimine moiety. Based on these results, the α-selective glycosylation reactions of these 3-aminodeoxy sugars and the structural modification of diosgenin were further investigated.