Abstract
Treatment of an α,β-unsaturated ketone and an aldehyde with chromium (II) chloride and R3SiCl in DMF gives cross-pinacol-type coupling products, 1,2-diols selectively. The anti/syn ratios of the produced 1,2-diols are shown to depend on the reaction temperature: At lower temperatures, the anti adduct is produced selectively, but at higher temperatures, the anti/syn ratios gradually decrease. When a combination of manganese and a catalytic amount of lead are used instead of chromium(II), 1,6-diketone, a dimer of the α,β-unsaturated ketone, is produced selectively.
Original language | English |
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Pages (from-to) | 17-23 |
Number of pages | 7 |
Journal | Chirality |
Volume | 15 |
Issue number | 1 |
DOIs | |
Publication status | Published - Jan 1 2003 |
Keywords
- 1,2-diol
- Chromium
- Manganese
- Pinacol-coupling
- Synthetic methods
ASJC Scopus subject areas
- Analytical Chemistry
- Catalysis
- Pharmacology
- Drug Discovery
- Spectroscopy
- Organic Chemistry