An Update of the Rules for Pyranoside Sulfonate Displacement

Karl J. Hale, Leslie Hough, Soraya Manaviazar, Andrew Calabrese

Research output: Contribution to journalLetter

34 Citations (Scopus)

Abstract

The 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.
Original languageEnglish
Pages (from-to)4838-4841
Number of pages4
JournalOrganic Letters
Volume16
Issue number18
Early online date12 Sep 2014
DOIs
Publication statusPublished - 2014

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Nucleophiles
sulfonates
Esters
Substitution reactions
Carbohydrates
Guidelines
Derivatives
nucleophiles
carbohydrates
viability
esters
substitutes
trifluoromethanesulfonic acid

Cite this

Hale, Karl J. ; Hough, Leslie ; Manaviazar, Soraya ; Calabrese, Andrew. / An Update of the Rules for Pyranoside Sulfonate Displacement. In: Organic Letters. 2014 ; Vol. 16, No. 18. pp. 4838-4841.
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An Update of the Rules for Pyranoside Sulfonate Displacement. / Hale, Karl J.; Hough, Leslie; Manaviazar, Soraya; Calabrese, Andrew.

In: Organic Letters, Vol. 16, No. 18, 2014, p. 4838-4841.

Research output: Contribution to journalLetter

TY - JOUR

T1 - An Update of the Rules for Pyranoside Sulfonate Displacement

AU - Hale, Karl J.

AU - Hough, Leslie

AU - Manaviazar, Soraya

AU - Calabrese, Andrew

PY - 2014

Y1 - 2014

N2 - The 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.

AB - The 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.

U2 - DOI:10.1021/ol502193j

DO - DOI:10.1021/ol502193j

M3 - Letter

VL - 16

SP - 4838

EP - 4841

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 18

ER -