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Microwave-Assisted Allylation of Acetals with Allyltrimethylsilane in the Presence of CuBr

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Michael E. Jung* and Andreas Maderna

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569 jung@chem.ucla.edu

J. Org. Chem., 2004, 69 (22), pp 7755–7757

DOI: 10.1021/jo049015w

Publication Date (Web): October 5, 2004

Section:

Aliphatic Compounds

Abstract

We describe the first synthesis of homoallyl ethers from acetals and allyltrimethylsilane using microwave heating and CuBr as a promoter. This method works best for aromatic acetals, giving the corresponding homoallyl ethers in good to quantitative yield.

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Gold-Catalyzed Formation of Oxonium Ions from Enynes and Their Intra- and Intermolecular Trapping with Allylsilanes
Jingwei Li, Xiaoguang Liu, and Daesung Lee
Organic Letters2012 14 (1), 410-413
- Gold-Catalyzed Formation of Oxonium Ions from Enynes and Their Intra- and Intermolecular Trapping with Allylsilanes
  Jingwei Li, Xiaoguang Liu, and Daesung Lee
  Organic Letters2012 14 (1), 410-413
  Gold-catalyzed ring closure of 1,5-enyne containing a silyl ether at the allylic position induces a skeletal rearrangement to form an oxonium intermediate, which then undergoes a smooth allylation in both an intra- and intermolecular manner. In the ...
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