DMP-mediated one-pot oxidative olefination of silyl ethers

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• 作者：Deng ; Guisheng ; Xu ; Baihua ; Liu ; Chunyu
• 关键词：Silyl ether ; Unsaturated ester ; Wittig reaction ; Dess– ; Martin periodinane ; One-pot method
• 刊名：Tetrahedron
• 出版年：2005
• 出版时间：June 13, 2005
• 年：2005
• 卷：61
• 期：24
• 页码：5818-5821
• 全文大小：202 K

文摘

Silyl ethers of arylic, allylic, propargylic and unactivated alcohols could be deprotected and oxidized with Dess–Martin periodinane, and the resulting aldehydes could be directly converted to the corresponding α,β-unsaturated esters in one pot with stabilized phosphoranes. Good selectivities were achieved upon a variety of protecting groups of alcohol by using this method. Other advantages of the protocol included simplicity of operations and high efficiency, as well as good to excellent yields.