Anzalone Peter W, Baru Ashvin R, Danielson Eric M, Hayes Patrick D, Nguyen Mai P, Panico Ambrose F, Smith Russell C, Mohan Ram S
Laboratory for Environment Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, Illinois 61701.
J Org Chem. 2005 Mar 18;70(6):2091-6. doi: 10.1021/jo048475m.
[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.
[反应：见正文] 已开发出三种由Bi(OTf)₃·xH₂O（1 < x < 4）催化将醛转化为高烯丙基醚的一锅法。高烯丙基醚的一锅合成既可以通过原位生成缩醛，然后使其与烯丙基三烷基硅烷反应来实现，也可以通过三组分合成来实现，即将醛、原甲酸三甲酯或烷氧基三甲基硅烷与烯丙基三甲基硅烷在三氟甲磺酸铋（0.1 - 1.0 mol%）存在下混合在一起。此外，还开发了一种高烯丙基乙酸酯的三组分合成方法，该方法是通过在三氟甲磺酸铋（3.0 - 5.0 mol%）存在下使醛、乙酸酐和烯丙基三甲基硅烷反应来实现的。使用相对无毒、易于操作且价格低廉的催化剂增加了这些方法的通用性。
