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4.4.40.22 Method 22: From Allyl Esters or Allyl Carbamates and a Silylcuprate Reagent

DOI: 10.1055/sos-SD-004-00909

Sarkar, T. K.Science of Synthesis, (20024863.

Allylsilanes are accessible by substitution reactions of allylic alcohol derivatives, such as allyl acetates, benzoates, and halides, with a (dimethylphenylsilyl)cuprate[‌142‌‌149‌] 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.[‌142‌‌144‌] (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]

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