Science of Synthesis

Sarkar, T. K., Science of Synthesis, (2002) 4, 843.

Silylation of lithiated alkenes generated by deprotonation of alkenes with butyllithium in the presence of N,N,N′,N′-tetramethylethylenediamine gives allylsilanes. The regioselectivity of this reaction depends on the deprotonation site of the alkene and the selectivity of attack of the allyllithium species on the halosilane. For methylenecyclobutane, a mixture of allylsilanes, for example, ‌20‌ and ‌21‌, forms, with the latter slightly favored (‌Scheme 12‌).[‌64‌] This method is suited for the preparation of a variety of terpenic allylsilanes, for example, silane ‌22‌.[‌65‌]

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References

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• 8.Meeeee-Meee, (8888) 88/8, 88.
• 8.Meeeee-Meee, (8888) M 88e, 8888.