Abstract
(Chemical Equation Presented) Three one-pot methods for the conversion of aldehydes to homoallyl ethers catalyzed by Bi(OTf)3• xH 2O (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 inflate (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.
Original language | English (US) |
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Pages (from-to) | 2091-2096 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 70 |
Issue number | 6 |
DOIs | |
State | Published - Mar 18 2005 |
Externally published | Yes |