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Updated: Jul 16, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Enantioselective 1,3-dipolar cycloadditions of diazoacetates with electron-deficient olefins
Mukund P Sibi1, Levi M Stanley, Takahiro Soeta
1Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105, USA. mukund.sibi@ndsu.edu
Abstract:
[reaction: see text] A general strategy for highly enantioselective 1,3-dipolar cycloaddition of diazoesters to beta-substituted, alpha-substituted, and alpha,beta-disubstituted alpha,beta-unsaturated pyrazolidinone imides is described. Cycloadditions utilizing less reactive alpha,beta-disubstituted dipolarophiles require elevated reaction temperatures, but still provide the corresponding pyrazolines with excellent enantioselectivities. Finally, an efficient synthesis of (-)-manzacidin A employing this cycloaddition methodology as a key step is illustrated.
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