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Please login to access the full content or check if you have access via4.4.40.22 Method 22: From Allyl Esters or Allyl Carbamates and a Silylcuprate Reagent
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Sarkar, T. K., Science of Synthesis, (2002) 4, 863.
Allylsilanes are accessible by substitution reactions of allylic alcohol derivatives, such as allyl acetates, benzoates, and halides, with a (dimethylphenylsilyl)cuprate[142–149] or related reagent.[150,151] Allyl carbamates are also amenable to this method, but, in this case, a modified protocol is used, involving the assemblage of a mixed (dimethylphenylsilyl)cuprate on the leaving group.[142–144] (Dimethylphenylsilyl)cuprate, used in this protocol, unfortunately has some undesirable features, including the formation of nonvolatile silicon-containing byproducts, both during preparation of the allylsilanes and in their subsequent reactions.[145] In spite of this, the dimethylphenylsilyl group is a good replacement for the trimethylsilyl group in practically all reactions of allylsilanes. Incidentally, use of mixed cuprates such as [(dimethylphenylsilyl)methyl]cuprate may eliminate or minimize silicon-containing byproducts and thereby improve the efficiency of the reaction.[145]
References
[142] | Meeeeee, M.; Meeeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
[143] | Meeeeee, M.; Meeeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
[144] | Meeeeee, M.; Meeeeee, M.; Meeeeeee, M. M.; Meeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[145] | Meeeeee, M.; Meeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[146] | Meeeeee, M.; Meeeee, M., Me., Meeeeeeee, (8888), 888. |
[147] | Meeeeee, M.; Meeeeee, M. M., M. Meeeeeeee. Meee., (8888) 888, 88. |
[148] | Meeeeee, M.; Meeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[149] | Meeeeee, M.; Meeeeeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[150] | Meeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[151] | Meeee, M.; Meeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |