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.