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Evidence of cation-coordination involvement in directing the regioselective di-inversion reaction of vicinal di-sulfonate esters

Hevey, Rachel and Ling, Chang-Chun. (2013) Evidence of cation-coordination involvement in directing the regioselective di-inversion reaction of vicinal di-sulfonate esters. Organic & Biomolecular Chemistry, 11 (11). pp. 1887-1895.

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Official URL: https://edoc.unibas.ch/70095/

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Abstract

Direct evidence has been obtained to confirm the unusual nucleophilic attack of an alkoxide at the S-center of sp(3)-hybridized sulfonyl esters. The unusual reaction pathway leads to S-O bond scission which is crucial for the regio- and stereoselective conversion of 2,3-di-O-sulfonates of 4,6-O-benzylidene-β-D-galactopyranosides into β-D-idopyranosides. In addition, strong evidence has been provided to clarify the role of the alkali counter-cation in the transformation. The cation is believed to influence the reaction rate via coordination to an oxygen in the sulfonate ester; the presence of a neighboring ring oxygen oriented in a cis-relationship greatly enhances reactivity of the sulfonyl ester.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Ehemalige Einheiten Pharmazie > Molekulare Pharmazie (Ernst)
05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Pharmazie > Molekulare Pharmazie (Ricklin)
UniBasel Contributors:Hevey, Rachel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
ISSN:1477-0520
e-ISSN:1477-0539
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:16 Nov 2020 11:13
Deposited On:16 Nov 2020 11:13

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