10.1021/acs.joc.8b02275.s001 Fenglin Chen Fenglin Chen Yanjiao Chen Yanjiao Chen Hongen Cao Hongen Cao Qing Xu Qing Xu Lei Yu Lei Yu Copper-Catalyzed Regioselective and Stereoselective Coupling of Grignard Reagents with Pent-1-en-4-yn-3-yl Benzoates: A Shortcut to (<i>Z</i>)<i>-</i>1,5-Disubstituted Pent-3-en-1-ynes from Accessible Starting Materials American Chemical Society 2018 generation -3-en Grignard reagents Pent -1-en Benzoates access henna Grignard Reagents alkynyl site stereoselective formation material Copper-Catalyzed Regioselective Disubstituted alkenyl allene products anti-inflammatory components pent -1-en benzoates Shortcut Materials Copper-catalyzed Accessible Stereoselective configured enynes disubstituted terminal alkenyl carbon bioactive regioselectively 2018-10-18 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Copper-Catalyzed_Regioselective_and_Stereoselective_Coupling_of_Grignard_Reagents_with_Pent-1-en-4-yn-3-yl_Benzoates_A_Shortcut_to_i_Z_i_i_-_i_1_5-Disubstituted_Pent-3-en-1-ynes_from_Accessible_Starting_Materials/7246763 Copper-catalyzed coupling of Grignard reagents with pent-1-en-4-yn-3-yl benzoates occurs regioselectively at the terminal alkenyl carbon rather than the alkynyl site, leading to the stereoselective formation of unexpected (<i>Z</i>)<i>-</i>1,5-disubstituted pent-3-en-1-ynes without generation of the initially expected alkenyl allene products. By using easily accessible starting materials, this reaction can provide direct access to thermodynamically unfavorable <i>Z</i>-configured enynes, which widely exist in many bioactive natural products, such as the anti-inflammatory components in henna.