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Issue 3, 2016
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Synthesis of enantiomerically pure bis(2,2-dimethyl-1,3-dioxolanylmethyl)chalcogenides and dichalcogenides

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Abstract

Herein we describe the reaction between the nucleophilic species of chalcogenium (sulfur, selenium and tellurium) and (R)- and (S)-solketal tosylates to prepare enantiomerically pure bis-1,3-dioxolanylmethyl chalcogenides and dichalcogenides in short reaction times and good yields. Furthermore, the new diselenide 4a was evaluated in the Michael reaction with acrylonitrile, giving (R)-3-[(2,3-dihydroxypropyl)selanyl]propanenitrile 6b after two steps.

Graphical abstract: Synthesis of enantiomerically pure bis(2,2-dimethyl-1,3-dioxolanylmethyl)chalcogenides and dichalcogenides

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Article information


Submitted
28 Oct 2015
Accepted
05 Jan 2016
First published
06 Jan 2016

New J. Chem., 2016,40, 2321-2326
Article type
Paper

Synthesis of enantiomerically pure bis(2,2-dimethyl-1,3-dioxolanylmethyl)chalcogenides and dichalcogenides

E. L. Borges, T. J. Peglow, M. S. Silva, C. G. Jacoby, P. H. Schneider, E. J. Lenardão, R. G. Jacob and G. Perin, New J. Chem., 2016, 40, 2321
DOI: 10.1039/C5NJ02945G

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