Abstract
Enantiomerically enriched thiiranium ion 5 has been prepared by silverassisted ionization of chloro sulfide 4 at -20°C. This thiiranium ion is configurationally stable in solution up to room temperature as demonstrated by the stereospecific capture of the ion by various oxygen- and nitrogen-based nucleophiles. Both isolated olefins and weak Lewis bases can promote the racemization of 5 but these processes can also be suppressed at low temperature. Capture of 5 by methanol is faster than the racemization processes.
Original language | English (US) |
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Pages (from-to) | 11737-11745 |
Number of pages | 9 |
Journal | Chemistry - A European Journal |
Volume | 15 |
Issue number | 43 |
DOIs | |
State | Published - Nov 2 2009 |
Keywords
- Episulfonium ions lewis bases
- Nucleophiles
- Stereoselectivity sulfur
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry