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Updated: Oct 3, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Stereodivergent synthesis of multi-substituted 1,3-dienes via tandem allylation/Peterson olefination
Qingbin Lu1, Ruibo Li1, Shengqiang Li1
1State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing, 210009, P. R. China. xuanyili@cpu.edu.cn.
Abstract:
We report a sequential copper-catalyzed branched-selective allyl addition and Peterson olefination. Branched selective allyl addition of allenylsilanes with ketones leads to anti-β-silyl homoallylic alcohols. In the presence of NaH, tri- and tetra-substituted 1,3-dienes are produced with Z-selectivity. The stereoselectivity is completely reversed under H2SO4 conditions.
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