Synthesis and Use of a Phosphoramidite Ligand for the Copper-Catalyzed Enantioselective Allylic Substitution. Tandem Allylic Substitution/Ring-Closing Metathesis
- 30 July 2004
- journal article
- psp
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 2004 (15) , 2586-2590
- https://doi.org/10.1055/s-2004-829188
Abstract
A new one-pot method of reductive amination is used to prepare a chiral C2 symmetrical amine. This amine is used for the synthesis of a new chiral phosphoramidite ligand. The new ligand is, in turn, used to illustrate the enantioselective copper-catalyzed allylic substitution with Grignard reagents. When a remote double bond is located on the Grignard reagent, the newly formed alkene undergoes an in situ ruthenium-catalyzed ring-closing metathesis to afford the cyclized product in 77% yield and 94% ee.Keywords
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