%0 Journal Article %A Chen, Fenglin %A Chen, Yanjiao %A Cao, Hongen %A Xu, Qing %A Yu, Lei %D 2018 %T Copper-Catalyzed Regioselective and Stereoselective Coupling of Grignard Reagents with Pent-1-en-4-yn-3-yl Benzoates: A Shortcut to (Z)-1,5-Disubstituted Pent-3-en-1-ynes from Accessible Starting Materials %U 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 %R 10.1021/acs.joc.8b02275.s001 %2 https://acs.figshare.com/ndownloader/files/13347242 %K generation %K -3-en %K Grignard reagents %K Pent -1-en Benzoates %K access %K henna %K Grignard Reagents %K alkynyl site %K stereoselective formation %K material %K Copper-Catalyzed Regioselective %K Disubstituted %K alkenyl allene products %K anti-inflammatory components %K pent -1-en benzoates %K Shortcut %K Materials Copper-catalyzed %K Accessible %K Stereoselective %K configured enynes %K disubstituted %K terminal alkenyl carbon %K bioactive %K regioselectively %X 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 (Z)-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 Z-configured enynes, which widely exist in many bioactive natural products, such as the anti-inflammatory components in henna. %I ACS Publications