| Title | Construction of cyclopenta[b]pyran-2-ones via chemoselective (3+2) cycloaddition between 2-pyrones and vinyl cyclopropanes |
| Authors | Liang, Xuefeng Ye, Weijian Thor, Waygen Sun, Lantian Wang, Bo He, Shuzhong Cheng, Yuen-Kit Lee, Chi-Sing |
| Affiliation | Peking Univ, Shenzhen Grad Sch, Lab Chem Genom, Lishui Rd, Shenzhen 518055, Peoples R China Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Hong Kong, Peoples R China Guizhou Univ, Sch Pharmaceut Sci, Guiyang 550025, Guizhou, Peoples R China |
| Keywords | DIASTEREOSELECTIVE SYNTHESIS ENANTIOSELECTIVE SYNTHESIS ALDEHYDES VINYLCYCLOPROPANES STEREOCHEMISTRY 3-NITROINDOLES CYCLOPENTANES REARRANGEMENT INDOLES IMINES |
| Issue Date | 21-Mar-2020 |
| Publisher | ORGANIC CHEMISTRY FRONTIERS |
| Abstract | A method for synthesising cyclopenta[b]pyran-2-ones through direct (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes is described. In the presence of Pd-2(dba)(3)/dppe in toluene, a series of 2-pyrones undergo chemoselective (3 + 2) cycloaddition with vinyl cyclopropanes and afford cyclopenta[b]pyran-2-ones in high yields (78-96%). The trans/cis ratio of the cycloadducts has been optimised up to 10 : 1. The proposed mechanism of this cycloaddition has been rationalised by computational studies. |
| URI | http://hdl.handle.net/20.500.11897/587220 |
| ISSN | 2052-4129 |
| DOI | 10.1039/d0qo00049c |
| Indexed | IC SCI(E) Scopus EI |
| Appears in Collections: | 深圳研究生院待认领 |
