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Synthesis 2004(15): 2586-2590
DOI: 10.1055/s-2004-829188
DOI: 10.1055/s-2004-829188
PSP
© Georg Thieme Verlag Stuttgart · New York
Synthesis and Use of a Phosphoramidite Ligand for the Copper-Catalyzed Enantioselective Allylic Substitution. Tandem Allylic Substitution/Ring-Closing Metathesis
Weitere Informationen
Received
26 April 2004
Publikationsdatum:
30. Juli 2004 (online)
Publikationsverlauf
Publikationsdatum:
30. Juli 2004 (online)
![](https://www.thieme-connect.de/media/synthesis/200415/lookinside/thumbnails/10.1055-s-2004-829188-1.jpg)
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.
Key words
allylic substitution - copper catalysis - ruthenium catalysis - enantioselectivity - Grignard reagents
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This compound is available from BASF AG on the following website: http://www.basf.de/en/produkte/chemikalien/interm/.
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