β-Selective C-Mannosylation of Electron-Rich Phenols

Abstract

The reaction of tetra-O-benzylmannosyl trichloroacet­imidate with electron-rich phenols in the presence of TMSOTf surprisingly leads to the exclusive formation of aryl β-C-glycosides while a preference for the α-anomer could be observed with other Lewis acids such as ZnCl₂.

Key words

glycosylation - phenols - C-glycosides - Lewis acids - anomers

References

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28

Compound 6 was first reported by Palmacci and Seeberger, who suggested the α-configuration. See ref. 14.

31

Compounds 10 and 12 were first reported by Li et al. who suggested the α-configuration. See ref. 16.