204578-86-9Relevant articles and documents
Enantioselective Reductive Homocoupling of Allylic Acetates Enabled by Dual Photoredox/Palladium Catalysis: Access to C2-Symmetrical 1,5-Dienes
Zhang, Hong-Hao,Tang, Menghan,Zhao, Jia-Jia,Song, Changhua,Yu, Shouyun
supporting information, p. 12836 - 12846 (2021/08/30)
Transition-metal-catalyzed reductive coupling reactions have emerged as powerful protocols to construct C-C bonds. However, the development of enantioselective C(sp3)-C(sp3) reductive coupling remains challenging. Herein, we report a highly regio-, diastereo-, and enantioselective reductive homocoupling of allylic acetates through cooperative palladium and photoredox catalysis using diisopropylethylamine or Hantzsch ester as a homogeneous organic reductant. This straightforward protocol enables the stereoselective construction of C(sp3)-C(sp3) bonds under mild reaction conditions. A series of C2-symmetrical chiral 1,5-dienes were easily prepared with excellent enantioselectivities (up to >99% ee), diastereoselectivities (up to >95:5 dr), and regioselectivities (up to >95:5 rr). The resultant chiral 1,5-dienes can be directly used as chiral ligands in asymmetric synthesis, and they can be also transformed into other valuable chiral ligands.
Palladium-iminophosphine-catalyzed homocoupling of alkynylstannanes and other organostannanes using allyl acetate or air as an oxidant
Shirakawa, Eiji,Nakao, Yoshiaki,Murota, Yasubumi,Hiyama, Tamejiro
, p. 132 - 136 (2007/10/03)
A palladium-iminophosphine complex was found to catalyze the homocoupling reaction of alkynylstannanes using allyl acetate as an oxidant, whereas aryl- and alkenylstannanes were oxidatively homocoupled with air.
PALLADIUM-CATALYZED COUPLING OF ALLYLIC ACETATES WITH ZINC
Sasaoka, Shin-ichi,Yamamoto, Taku,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi
, p. 315 - 318 (2007/10/02)
Allylic acetates were coupled with zinc dust in the presence of a catalytic amount of to give the corresponding 1,5-dienes under mild conditions in high yields.Significant cosolvent effects were found with methanol or 1,2-ethanediol in tetrahydrofuran.