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A novel synthesis of β-ketosilanes via organoboranes

✍ Scribed by Narayan G Bhat; Chris Martinez; J De Los Santos

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
138 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

A convenient, novel synthesis of b-ketosilanes based on (Z)-1-bromo-1-alkenylboronate esters is developed. a-Bromo-(Z)-1-alkenylboronate esters readily available using literature procedures smoothly undergo a reaction with trimethylsilylmethyllithium in tetrahydrofuran to provide the corresponding ate' complexes. These ate' complexes will undergo intramolecular nucleophilic substitution reactions to aord the corresponding (E)-trisubstituted ole®ns containing trimethylsilylmethyl moiety. The oxidation of these intermediates with sodium acetate and hydrogen peroxide provides b-ketosilanes in good yields (63±75% yield).

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