Related Experiment Video
Updated: Apr 5, 2026
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Asymmetric Alkene Boration and Z-Retentive Allylic Substitution Reactions under Cu/Pd Relay Catalysis
Wen-Bin Cao1, Guo-Ming Yu1, Jiandong Liu1
1New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
Abstract:
Cu/Pd-cocatalyzed cascade asymmetric alkene boration and Z-retentive allylic substitution reactions are described. Taking advantage of palladium catalysts that well tune the rates of both the π-σ-π isomerization process of the π-allyl-palladium species and nucleophilic substitution, either Z-retentive or Z-to-E allylic substitution reactions can be achieved, with alkyl copper nucleophiles generated in situ via Cu-catalyzed alkene boration. Chiral Z- and E-olefins containing an organoboronate functional group are afforded under Cu/Pd relay catalysis from the same starting materials. Both reactions proceed with high yields (up to 95%), excellent Z/E ratios (up to >19:1), and good enantioselectivity (up to 94% ee).
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