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Updated: Feb 11, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Serial [5+2]/[4+2] Cycloadditions: Facile, Preparative, Multi-Component Syntheses of Polycyclic Compounds from
Paul A Wender1, Gabriel G Gamber1, Marc J C Scanio1
1Department of Chemistry, Stanford University Stanford, CA 94305-5080 (USA) Fax: (+1) 650-725-0259.
This study introduces a new reaction forming four bonds and stereocenters to create complex bicyclo[5.4.0]undecane derivatives from simple starting materials in one step.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Bicyclo[5.4.0]undecane derivatives are important structural motifs.
- Efficient synthesis of complex organic molecules is a key challenge in chemistry.
Purpose of the Study:
- To develop a novel synthetic route for bicyclo[5.4.0]undecane derivatives.
- To achieve the formation of multiple bonds and stereocenters in a single operation.
Main Methods:
- A one-step reaction protocol was employed.
- The reaction utilizes readily available starting materials.
Main Results:
- Formation of four new bonds and up to four new stereocenters.
- Successful synthesis of complex bicyclo[5.4.0]undecane derivatives.
- Demonstration of preparative scale feasibility (100 mmol).
Conclusions:
- The developed reaction offers an efficient method for synthesizing complex bicyclo[5.4.0]undecane structures.
- The single-step, preparative-scale capability makes this a valuable synthetic tool.
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