Back to Search
Start Over
Chiral phosphinoazomethinylate salts as new ‘one-step available’ ligands for copper-catalyzed asymmetric conjugate addition
- Source :
- Tetrahedron: Asymmetry, Tetrahedron: Asymmetry, 2008, 19 (15), pp.1804-1809. ⟨10.1016/j.tetasy.2008.07.011⟩, Tetrahedron: Asymmetry, Elsevier, 2008, 19, pp.1804-1809. ⟨10.1016/j.tetasy.2008.07.011⟩, Tetrahedron: Asymmetry, Elsevier, 2008, 19 (15), pp.1804-1809. ⟨10.1016/j.tetasy.2008.07.011⟩, Tetrahedron: Asymmetry, 2008, 19, pp.1804-1809. ⟨10.1016/j.tetasy.2008.07.011⟩
- Publication Year :
- 2008
- Publisher :
- Elsevier BV, 2008.
-
Abstract
- Herein, we report the use of phosphinoazomethinylate salts as chiral efficient ligands for the copper-catalyzed asymmetric conjugate addition (ACA) of dialkylzinc to various enones. These tridentate P,N,O ligands are straightforwardly obtained in a one-step procedure from commercially available enantiopure α-aminoacids. Performing the conjugate addition in the greener AcOEt solvent, high enantioselectivities were reached for both cyclic and acyclic enones ranging between 72% to 98% ee and 96% to >99%, respectively. The 2/1 Cu/ligand ratio required to obtain high enantioselectivities, led us to envisage a copper–copper bi-metallic catalytic system for this transformation.
- Subjects :
- [CHIM.ORGA]Chemical Sciences/Organic chemistry
010405 organic chemistry
Chemistry
Ligand
Organic Chemistry
One-Step
[CHIM.CATA]Chemical Sciences/Catalysis
010402 general chemistry
01 natural sciences
Combinatorial chemistry
Catalysis
0104 chemical sciences
Inorganic Chemistry
Solvent
Enantiopure drug
Copper catalyzed
[CHIM]Chemical Sciences
Organic chemistry
Physical and Theoretical Chemistry
ComputingMilieux_MISCELLANEOUS
Conjugate
Subjects
Details
- ISSN :
- 09574166
- Volume :
- 19
- Database :
- OpenAIRE
- Journal :
- Tetrahedron: Asymmetry
- Accession number :
- edsair.doi.dedup.....83f89c8fcdca1ec44300cd8170653a44