A new method for the preparation of /Schloro and j3-bromo-a$unsaturated ketones from pdiketones is described. Utilizing Vilsmeier reagents (preparedfrom N, N-dimethylformamide and oxalyl chloride or oxalyl bromide} /3-halo-a&nsaturated ketones are isolated in excellent yields.
Novel syntheses of β-halo-α,β-unsaturated ketones
✍ Scribed by Michael H Kress; Yoshito Kishi
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- French
- Weight
- 149 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0040-4039
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## Abstract For Abstract see ChemInform Abstract in Full Text.
BIRCH' demonstrated in 1950 that a steroidal a,p-unsaturated ketone (I) may be deconjugated to its p,y-unsaturated ketone isomer (III) by irreversible protonation of the conjugate anion (II), however, the requisite anion has been prepared only by indirect means (e.g. through the enol acetate, 132 fr
Akstra~. ~l~-Unsaturated ketones are aziridinated by [(arenesulphonyl)oxy]carbamates and CaO (or Cs2CO3) or by N3CO2Et photolysis. A remote chiral center induced up m 74% ~e. Bis-unsaturated subeuates showed scarce regioselectivity under all conditions.