Studies have been carried out on the addition of trimethylsilylcyanide to aldehydes using highly active chiral lithium phenolate catalysts. The screening of a number of chiral phenolates has resulted in a system which gives the TMS ethers of cyanohydrins in excellent chemical yields with enantiomeri
The asymmetric addition of trimethylsilylcyanide to aldehydes catalysed by anionic chiral nucleophiles. Part 1
β Scribed by Ian P Holmes; Henri B Kagan
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 87 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Trimethylsilylcyanide has been added to a number of aldehydes using a highly active chiral catalyst. This procedure gives the TMS ethers of the corresponding cyanohydrins in excellent chemical yields with enantiomeric excesses of up to 59%. The reaction is believed to occur through hypervalent silicon intermediates.
π SIMILAR VOLUMES
The use of a bimetallic titanium salen complex as a catalyst for the asymmetric addition of trimethylsilylcyanide to ketones is reported. The cyanohydrin trimethyisilyl ethers are obtained with enantiomeric excesses of up to 72% from reactions carried out at room temperature and atmospheric pressure