| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5225245 | Tetrahedron | 2009 | 13 Pages |
A convenient method for the synthesis of optically active dialkyl diselenides derived from bicyclic terpenes functionalized with hydroxy, etheral, sulfide, and selenide groups is described. The diselenides were used for a synthesis of chiral electrophilic selenium reagents, then in the asymmetric selenenylation of styrene and selenocyclization with o-allylphenol. The influence of nonbonding selenium-heteroatom interactions in the generated organoselenium electrophiles on the stereoselectivity of an addition reaction has been investigated. Calculations by a DFT method on a B3LYP (6–311G (d)) level, confirmed the existence of nonbonded selenium–heteroatom interactions in the investigated systems.
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