Kinetic resolution of secondary alcohols using proline-derived bicyclic iminium salts

✍ Scribed by R. Alan Aitken; Karamat ali; Shaun T.E. Mesher

• Book ID: 104257176
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 280 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00815-0

✦ Synopsis

Abstracti 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 efticiencly with sodium I-phenylethoxide in toluene at RT where either 3 or the benxyl salt 14 give e.e.s of Z-255 and changing the heteroatoms present in the salts, the metal cation used and the solvent and temperature aII give similar or lower selectivity.