Issue 3, 2016

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

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

Supplementary files

Article information

Article type
Paper
Submitted
28 Oct 2015
Accepted
05 Jan 2016
First published
06 Jan 2016

New J. Chem., 2016,40, 2321-2326

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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