Abstract
Some camphor-derived vinyl sulfones bearing oxygen functionality at the allylic position have been synthesized and their nucleophilic epoxidation reactions under Meth-Cohn conditions have been explored. The γ-oxygenated camphor-derived vinyl sulfones underwent mildly diastereoselective nucleophilic epoxidation reactions, affording the derived sulfonyloxiranes in up to 5.8:1 dr. The observed diastereoselectivities were sensitive to the reaction conditions employed. In contrast, no stereoselectivity was observed in the nucleophilic epoxidation of the corresponding γ-oxygenated isobornyl vinyl sulfone. A tentative mechanism has been proposed to explain the origins of the diastereoselectivity
| Original language | English |
|---|---|
| Pages (from-to) | 643-649 |
| Journal | Tetrahedron Asymmetry |
| Volume | 23 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2012 |