%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