Department of Chemistry and Biochemistry, Miami University, Oxford, Ohio 45056, USA.
Chemistry. 2010 Jan 11;16(2):639-44. doi: 10.1002/chem.200902185.
Macrocyclic propargyl acetates containing a furan ring were prepared by using a CrCl(2)-promoted reaction. In the presence of either a Au(I) or Au(III) catalyst, a tandem 3,3-rearrangement/transannular [4+3] cycloaddition reaction occurred to give propargyl acetates that are regio- and diastereospecific. The regiochemistry of the product is controlled by the position of the acetoxy group in the starting material and the stereochemistry of the reaction depends on the ring size.
通过使用 CrCl(2)促进的反应，制备了含有呋喃环的大环丙炔基乙酸酯。在 Au(I)或 Au(III)催化剂的存在下，发生串联的 3,3-重排/环加成反应，得到丙炔基乙酸酯，具有区域和立体选择性。产物的区域化学由起始原料中乙酰氧基的位置控制，反应的立体化学取决于环的大小。
