ZnI2-Mediated Cyanomethyl Ether Synthesis from MEM Ethers with Trimethylsilyl Cyanide

초록

A highly practical protocol for preparing cyanomethyl ethers from aliphatic alcohols via their MEM ethers has been developed using trimethylsilyl cyanide in the presence of a Lewis acid. A number of Lewis acids were investigated, and ZnI2 was found to be the most effective for converting a variety of MEM ethers to the corresponding cyanomethyl ethers. Both bidentate coordination of ZnI2 with the MEM group and steric hindrance of the substrates play pivotal roles in this transformation.

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