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Updated: Aug 16, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Catalytic asymmetric synthesis with rh-diene complexes: 1,4-addition of arylboronic acids to unsaturated esters
Jean-François Paquin1, Corey R J Stephenson, Christian Defieber
1Laboratorium für Organische Chemie, ETH Hönggerberg, HCI H335, 8093 Zürich, Switzerland.
Abstract:
A general route to enantioenriched tert-butyl 3,3-diarylpropanoates is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to unsaturated tert-butyl esters in the presence of chiral dienes as ligands. The addition of both electron-poor and electron-rich boronic acids proceeds smoothly with various enoates in 63-90% yield with high enantioselectivites (89-94% ee). [reaction: see text]
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