Kinetic Resolution of Secondary Alcohols Using Proline-Derived Bicyclic Iminium Salts

Robert Alan Aitken, K Ali, ST Mesher

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

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 languageEnglish
Pages (from-to)4179-4182
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number23
Publication statusPublished - 9 Jun 1997

Fingerprint

Dive into the research topics of 'Kinetic Resolution of Secondary Alcohols Using Proline-Derived Bicyclic Iminium Salts'. Together they form a unique fingerprint.

Cite this