Sitian Yuan, Hongwei Zhou, Liang Gao
Jan 11, 2018
Citations
0
Influential Citations
21
Citations
Journal
Organic letters
Abstract
A regioselective 2,4-dibromohydration of conjugated enynes is reported for the synthesis of 2-(2,4-dibromobut-2-enoyl)benzoate. In the presence of tetra-n-butylammonium bromide and H2O the transformation proceeds smoothly with good reaction efficiency and a broad reaction scope. Mechanism studies indicate that the neighboring ester group participates in the 2,4-dibromohydration, and the oxygen atom of ester is transferred into the C-C triple bond to form the keto carbonyl group in the product. 2-(2,4-Dibromobut-2-enoyl)benzoate is recognized as an important synthon toward phthalazin-1(2H)-one and the natural product Shihunine.