Cerium(IV) Ammonium Nitrate (CAN): A Very Efficient Reagent for the Synthesis of Tertiary Ethers
作者:E. Alvarez-Manzaneda、R. Chaboun、E. Alvarez、E. Cabrera、R. Alvarez-Manzaneda、A. Haidour、J. Ramos
DOI:10.1055/s-2006-947356
日期:2006.8
Treatment of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature led to the corresponding tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Utilizing this methodology, manoyl oxide (25a) and a variety of fragrant compounds, such as linalool oxide (8), caparrapi oxide (12), ambrox (14) and other related amber-gris-type odorants have been synthesized; 16 examples are described.
在室温下用硝酸铈铵处理叔1,4-和1,5-二醇可以高产率和立体选择性地生成相应的四氢呋喃和四氢吡喃衍生物。利用该方法,合成了氧化甘露醇(25a)和多种芳香化合物,如氧化芳樟醇(8)、氧化卡帕拉皮(12)、降龙涎香醚(14)和其他相关的灰琥珀型气味剂;描述了 16 个示例。