Solvent effects in the nucleophilic substitutions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate: Trichloroethylene as solvent for stereoselective C - And O-glycosylations

Joanna C. Kendale; Elizabeth M. Valentín; K. A. Woerpel

doi:10.1021/ol501471c

Solvent effects in the nucleophilic substitutions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate: Trichloroethylene as solvent for stereoselective C - And O-glycosylations

Joanna C. Kendale, Elizabeth M. Valentín, K. A. Woerpel

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of S_N1 products, while nonpolar solvents favor S_N2 products. Trichloroethylene was identified as the solvent most likely to give S_N2 products in both C- and O-glycosylation reactions.

Original language	English (US)
Pages (from-to)	3684-3687
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	14
DOIs	https://doi.org/10.1021/ol501471c
State	Published - Jul 18 2014

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Solvent effects in the nucleophilic substitutions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate: Trichloroethylene as solvent for stereoselective C - And O-glycosylations. / Kendale, Joanna C.; Valentín, Elizabeth M.; Woerpel, K. A.
In: Organic Letters, Vol. 16, No. 14, 18.07.2014, p. 3684-3687.

Research output: Contribution to journal › Article › peer-review

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Solvent effects in the nucleophilic substitutions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate: Trichloroethylene as solvent for stereoselective C - And O-glycosylations

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