An Update of the Rules for Pyranoside Sulfonate Displacement
2014; American Chemical Society; Volume: 16; Issue: 18 Linguagem: Inglês
10.1021/ol502193j
ISSN1523-7060
AutoresKarl J. Hale, L. Hough, Soraya Manaviazar, Andrew Calabrese,
Tópico(s)Polyamine Metabolism and Applications
ResumoThe original 1967 Richardson-Hough rules for predicting SN2 displacement viability in carbohydrate sulfonate derivatives with external nucleophiles have now been updated. Not only do the original rules still hold, but the newly updated rules rationalize why O-triflates (trifluoromethanesulfonate esters) frequently allow many seemingly "disallowed" pyranosidic nucleophilic substitutions to proceed. The new guidelines, which are based on three decades of experimental evidence, allow the feasibility of many pyranosidic O-triflate SN2 displacements to be gauged beforehand.
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