An Update of the Rules for Pyranoside Sulfonate Displacement

作者:Hale Karl J*; Hough Leslie; Manaviazar Soraya; Calabrese Andrew
来源:Organic Letters, 2014, 16(18): 4838-4841.
DOI:10.1021/ol502193j

摘要

The original 1967 Richardson Hough rules for predicting S(N)2 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 %26quot;disallowed%26quot; 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 S(N)2 displacements to be gauged beforehand.

  • 出版日期2014-9-19