Upon condensation of 6-thio-6-deoxy-mannosyl donors 1,2-cis products are obtained with a high degree of stereoselectivity. Subsequent reductive removal of the 6-thio functionality gives 1,2-cisrhamnosides. The 1,2-cis-selectivity can be rationalized with a product forming 3H4-oxocarbenium, which is in equilibrium with a bridged sulfonium intermediate.
A. E. Christina, D. V. D. Es, J. Dinkelaar, H. S. Overkleeft, G. A. V. D. Marel and J. D. C. Codée, Chem. Commun., 2012, 48, 2686 DOI: 10.1039/C2CC17623H
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