Synthesis and Use of a Phosphoramidite Ligand for the Copper-Catalyzed Enantioselective­ Allylic Substitution. Tandem Allylic Substitution/Ring-Closing­ Metathesis

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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