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Updated: Aug 1, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate
S Lai1, C K Zercher, J P Jasinski
1Department of Chemistry, University of New Hampshire, Durham, NH 03824, USA.
Abstract:
A tandem chain extension-aldol reaction was developed in which beta-keto esters are transformed to alpha-substituted-gamma-keto esters in an efficient zinc-mediated, one-pot reaction. The diastereoselectivity of the reaction ranged from good to excellent with syn stereochemistry observed for beta-keto ester and amide substrates and anti-stereochemistry observed for a beta-keto imide. [reaction: see text]
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