The directed lithiation of some 3-acylchromone acetals
β Scribed by G.Elena Daia; Christopher D. Gabbutt; John D. Hepworth; B.Mark Heron; David E. Hibbs; Michael B. Hursthouse
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 228 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
3-Acylchromone acetals are lithiated at C-2. Subsequent electrophilic trapping gives chtomones 4 together with a ting-conwacted rimer 6. During the formation of some acetals, an acidcatalysed rearrangement to a 2-substituted 3-fotmylchromone acetal is observed.
π SIMILAR VOLUMES
The dimethylacetal of benzaldehyde and some 3, 3,4 and 3,4,5 oxygenated derivatives thereof are regiospecifically deprotonated at the 2-position by alkyl lithiums. The resulting aryl lithiums provide various 2-substituted benzaldehydes in moderate to excellent yields. Following the pioneering work
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1-(Triisopropylsilyl)indole can be directly lithiated at 3-position with tert-BuLi-TMEDA in hexane at 0Β°C for 3 h. The generated lithio species is reacted with a variety of electrophiles to give 3-substituted 1-(triisopropylsilyl)indoles in good yields.