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Updated: Jan 8, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Enantioselective Alkyne-Mediated Aldehyde Allylation of Alcohol Proelectrophiles Using RuHCl(CO)(PPh3)3 as
Madeline M Evarts1, Thien-Quang N Nguyen1, Michael J Krische1
1University of Texas at Austin, Department of Chemistry, Austin, Texas 78712, United States.
Abstract:
The catalyst assembled from inexpensive RuHCl(CO)(PPh3)3, JOSIPHOS (SL-J009-1), and either NaI or KI affects anti-diastereo- and enantioselective alkyne-mediated allylation of alcohol proelectrophiles via hydrogen autotransfer. This protocol offers an alternative to the iodide-bound precatalyst RuI(CO)3(η3-C3H5), which is somewhat sensitive and not commercially available. Application to the asymmetric synthesis of cis-2,3-disubstituted pyrrolidines 5a-5c and cis-2,3-disubstituted azetidine 6 is described.
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