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Intramolecular [2+2] Cycloaddition Reactions of Alkynyl Ether Derived Ketenes. A Convenient Synthesis of Donor-Acceptor Cyclobutanes

  作者 TRAN VINCENT; MINEHAN THOMAS G  
  选自 期刊  Organic Letters;  卷期  2011年13-24;  页码  6588-6591  
  关联知识点  
 

[摘要]Mild thermolysis of tert-butyl alkynyl ethers furnishes aldoketenes, which undergo facile [2 + 2] cycloaddition reactions with pendant di- and trisubstituted alkenes. A wide variety of cis-fused cyclobutanones are produced in moderate to high diastereoselectivity and good to excellent yields by this method, and free hydroxyl groups are tolerated in the ene-ynol ether starting materials. Enol-ynol ethers also undergo efficient reaction to produce donor acceptor cyclobutanes in high yields.

 
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