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Updated: Nov 1, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Iridium-catalyzed enantioselective olefinic C(sp2)-H allylic alkylation
Rahul Sarkar1, Santanu Mukherjee1
1Department of Organic Chemistry, Indian Institute of Science Bangalore 560 012 India sm@iisc.ac.in +91-80-2360-0529 +91-80-2293-2850.
Abstract:
The first iridium-catalyzed enantioselective olefinic C(sp2)-H allylic alkylation is developed in cooperation with Lewis base catalysis. This reaction, catalyzed by cinchonidine and an in situ generated cyclometalated Ir(i)/phosphoramidite complex, makes use of the latent enolate character of an α,β-unsaturated carbonyl compound, namely coumalate ester, to introduce an allyl group at its α-position in a branched-selective manner in moderate to good yield with good to excellent enantioselectivities (up to 98 : 2 er).
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