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Updated: Jan 22, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Iridium-Catalyzed Enantioselective Allylic Substitution with Aqueous Solutions of Nucleophiles
Tobias Sandmeier1, F Wieland Goetzke1, Simon Krautwald1
1ETH Zürich , Vladimir-Prelog-Weg 3 , HCI, 8093 Zürich , Switzerland.
Abstract:
The iridium-catalyzed asymmetric allylic substitution under biphasic conditions is reported. This approach allows the use of various unstable and/or volatile nucleophiles including hydrazines, methylamine, t-butyl hydroperoxide, N-hydroxylamine, α-chloroacetaldehyde and glutaraldehyde. This transformation provides rapid access to a broad range of products from simple starting materials in good yields and up to >99% ee and 20:1 d.r. Additionally, these products can be elaborated efficiently into a diverse set of cyclic and acyclic compounds, bearing up to four stereocenters.
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