Abstract
The proline-derived bicyclic iminium salt 3 can be used to bring about kinetic resolution in its reaction with salts of secondary alcohols to give the corresponding methyl sulfides. Reaction proceeds most efficiently with sodium 1-phenylethoxide in toluene at RT where either 3 or the benzyl salt 14 give e.e.s of 21-25% and changing the heteroatoms present in the sails, the metal cation used and the solvent and temperature all give similar or lower selectivity. (C) 1997 Elsevier Science Ltd.
| Original language | English |
|---|---|
| Pages (from-to) | 4179-4182 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 38 |
| Issue number | 23 |
| Publication status | Published - 9 Jun 1997 |