Indium(I) bromide-mediated bromocyanomethylation of carbonyl compounds
✍ Scribed by J.A. Nóbrega; Simone M.C. Gonçalves; C. Peppe
- Book ID
- 104210601
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 149 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Bromocyanomethylation of a variety of carbonyl compounds to produce the corresponding 2-bromo-3hydroxynitriles has been achieved in moderate to good yields by the action of dibromoacetonitrile and indium(I) bromide. Moderate diastereoselectivity was observed. Exclusive mono-coupling at the carbonyl group was found with 1,2-diketones and a-haloketones.
📜 SIMILAR VOLUMES
Carbonyl compounds were efficiently transformed into their corresponding 2,2-dichloro-3-hydroxynitrile derivatives by the action of trichloroacetonitrile and indium(I) bromide.
Anomalous syn-diastereoselectivity of indium-mediated coupling of aldehydes with bromides Z-3b and E-3b is reported. The reaction afforded high syn selectivity regardless of the allylic bromide geometry. Preliminary studies on the enantioselective indium-mediated allylation were attempted and found
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