Departament de Química Orgànica, Facultat de Química, Universitat de València , C/Dr. Moliner 50, E-46100 Burjassot, València, Spain.
Org Lett. 2016 Aug 5;18(15):3538-41. doi: 10.1021/acs.orglett.6b01494. Epub 2016 Jul 15.
The enantioselective conjugate alkynylation of β-aryl-β-trifluoromethyl enones has been carried out using terminal alkynes and diethylzinc in the presence of 3,3'-bis(perfluorophenyl)BINOL as the chiral ligand to give the corresponding ketones bearing a trifluoromethylated propargylic quaternary stereocenter with fair to good enantioselectivities. Enones bearing a bulky 2-naphthyl attached to the carbonyl group provided the best enantioselectivities. The synthetic applicability of the resulting products has been demonstrated with their iodocyclization to form 4H-pyrans.
β-芳基-β-三氟甲基烯酮的对映选择性共轭炔基化反应已经在 3,3′-双（全氟苯基）BINOL 作为手性配体的存在下，使用末端炔烃和二乙基锌进行了研究，得到了相应的酮，其中含有一个带有三氟甲基化丙炔基季立体中心，具有中等至良好的对映选择性。在羰基上连接有大体积的 2-萘基的烯酮提供了最佳的对映选择性。通过碘环化形成 4H-吡喃来证明了所得产物的合成适用性。
