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Updated: Jun 26, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Desymmetrization of Cyclic Sulfonimidamides by Asymmetric Allylation
David A Gutierrez1, Garrett Toth-Williams1, Croix J Laconsay2
1Department of Chemistry, University of California, Davis, One Shields Ave., Davis California, 95616, United States.
Abstract:
Herein we report the first transition metal-catalyzed approach to the enantioenriched synthesis of cyclic sulfonimidamides relying on commercially available palladium catalysts and ligands. High-throughput experimentation (HTE) was employed to identify the optimal catalyst system and solvent. The method is applied to a variety of saturated and unsaturated rings and exhibits the highest selectivity for 2-substituted allyl electrophiles. The products are further elaborated to complex, tricyclic scaffolds. DFT experiments presented herein highlight the key ligand substrate interactions leading to the high levels of enantioselectivity.
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