Facile generation of α-silyl carbanion of trimethylsilyl group assisted by intramolecular pyridyl group coordination
1999; Elsevier BV; Volume: 40; Issue: 30 Linguagem: Inglês
10.1016/s0040-4039(99)01027-8
ISSN1873-3581
AutoresKenichiro Itami, Koichi Mitsudo, Jun‐ichi Yoshida,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoNovel methodology for the generation of α-silyl carbanion by the deprotonation of trimethylsilyl group with tert-butyllithium or LDA has been developed. This newly developed α-lithiation protocol is based on the intramolecular pyridyl group coordination to stabilize the α-silyl carbanion, together with the inherent silicon α effect. The importance of the use of the 2-pyridyl group in ‘pyridyl’- and ‘silyl’-directed α-lithiation has been confirmed by the control experiments utilizing phenyltrimethylsilane and (3-pyridyl)trimethylsilane.
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