Solvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations | Zendy

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

Open Access

Solvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations

Author(s) -

Joanna C. Kendale,

Elizabeth M. Valentín,

K. A. Woerpel

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol501471c

Subject(s) - chemistry , trimethylsilyl trifluoromethanesulfonate , stereoselectivity , tetrahydropyran , solvent , nucleophile , trimethylsilyl , trifluoromethanesulfonate , trichloroethylene , organic chemistry , catalysis , ring (chemistry)

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(N)1 products, while nonpolar solvents favor S(N)2 products. Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research