Journal
TETRAHEDRON-ASYMMETRY
Volume 19, Issue 10, Pages 1237-1244Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2008.04.027
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A convenient route for the synthesis of optically active dialkyl diselenides from the p-menthane system utilizing a reaction of alkyl tosylates and chlorides with sodium diselenide is reported. The diselenides obtained have been used for asymmetric methoxyselenenylation of styrene. Quantum chemical calculations of the chair conformers stability of the terpeneselenenyl bromides from the p-menthane group have also been carried out using density functional theory (DFF, at the B3LYP/6-311G(d) level). The influence of the diselenides structure on the stereoselectivity in the methoxyselenenylation reaction is also discussed. (C) 2008 Elsevier Ltd. All rights reserved.
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