Related Experiment Video
Updated: May 14, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Copper-catalyzed enantioselective allyl-allyl cross-coupling
Valentín Hornillos1, Manuel Pérez, Martín Fañanás-Mastral
1Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Researchers developed a novel copper(I)-phosphoramidite catalyst for asymmetric allyl-allyl cross-coupling reactions. This method achieves high enantioselectivity and works with diverse functionalized substrates, aiding in complex molecule synthesis.
Area of Science:
- Organic Chemistry
- Catalysis
- Asymmetric Synthesis
Background:
- Allyl-allyl cross-coupling is a crucial reaction in organic synthesis.
- Developing enantioselective methods for this transformation remains a significant challenge.
- Copper catalysis offers a versatile platform for developing new synthetic methodologies.
Purpose of the Study:
- To develop a novel catalytic system for asymmetric allyl-allyl cross-coupling.
- To achieve high enantioselectivity in the cross-coupling reaction.
- To demonstrate the broad substrate scope and utility in complex molecule synthesis.
Main Methods:
- Utilized a copper(I)-phosphoramidite catalytic system.
- Investigated asymmetric allyl-allyl cross-coupling reactions.
- Employed various functionalized substrates to assess reaction scope.
Main Results:
- Achieved high enantioselectivity in the asymmetric allyl-allyl cross-coupling.
- Demonstrated tolerance for a wide range of functionalized substrates.
- Successfully applied the methodology to the synthesis of a Martinelline alkaloids chromene derivative core.
Conclusions:
- The developed Cu(I)-phosphoramidite catalyst is effective for asymmetric allyl-allyl cross-coupling.
- The reaction exhibits broad functional group tolerance and high enantioselectivity.
- This method provides a versatile route for synthesizing complex molecules, including natural product cores.
Related Concept Videos
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Crossed Aldol Reactions: Overview
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction
