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Updated: Jul 10, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Experimental and Computational Studies for the Synthesis of Functionalized Cyclopropanes from 2-Substituted Allylic
Chengtao Zhao1, Tatiana Besset1, Claude Y Legault2
1INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), Normandie Univ., 76000, Rouen, France.
Abstract:
The catalytic asymmetric synthesis of highly functionalized cyclopropanes from 2-substituted allylic derivatives is reported. Using ethyl diazo acetate, the reaction, catalyzed by a chiral ruthenium complex (Ru(II)-Pheox), furnished the corresponding easily separable cis and trans cyclopropanes in moderate to high yields (32-97 %) and excellent ee (86-99 %). This approach significantly extends the portfolio of accessible enantioenriched cyclopropanes from an underexplored class of olefins. DFT calculations suggest that an outer-sphere mechanism is operative in this system.
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