✦ LIBER ✦
Facile generation of α-silyl carbanion of trimethylsilyl group assisted by intramolecular pyridyl group coordination
✍ Scribed by Kenichiro Itami; Koichi Mitsudo; Jun-ichi Yoshida
- Book ID
- 104261810
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 212 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Novel methodology for the generation of ct-silyl carbanion by the deprotonation of trimethylsilyl group with tertbutyllithium or LDA has been developed. This newly developed ct-lithiation protocol is based on the intramolecular pyridyl group coordination to stabilize the 0t-silyl carbanion, together with the inherent silicon 0t effect. The importance of the use of the 2-pyridyl group in 'pyridyl'-and 'silyl'-directed 0t-lithiation has been confirmed by the control experiments utilizing phenyltrimethylsilane and (3-pyridyl)trimethylsilane.