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J Org Chem ; 70(6): 2091-6, 2005 Mar 18.
Artículo en Inglés | MEDLINE | ID: mdl-15760192

RESUMEN

[reaction: see text] Three one-pot methods for the conversion of aldehydes to homoallyl ethers catalyzed by Bi(OTf)(3).xH(2)O (1 < x < 4) have been developed. The one-pot synthesis of homoallyl ethers can be achieved either by in situ generation of the acetal followed by its reaction with allyltrialkylsilane or by a three-component synthesis in which the aldehyde, trimethylorthoformate or an alkoxytrimethylsilane and allyltrimethylsilane are mixed together in the presence of bismuth triflate (0.1-1.0 mol %). In addition, a three-component synthesis of homoallyl acetates, which is achieved by reacting the aldehyde, acetic anhydride, and allyltrimethylsilane in the presence of bismuth triflate (3.0-5.0 mol %), has been developed. The use of a relatively nontoxic, easy to handle, and inexpensive catalyst adds to the versatility of these methods.


Asunto(s)
Acetatos/síntesis química , Aldehídos/química , Compuestos Alílicos/química , Ésteres/síntesis química , Mesilatos/química , Compuestos Organometálicos/química , Aldehídos/síntesis química , Compuestos Alílicos/síntesis química , Catálisis , Conformación Molecular
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