Chiral Lithium Amido Aryl Zincates: Simple and Efficient Chemo‐ and Enantio‐Selective Aryl Transfer Reagents |
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Authors: | Pauline Chaumont‐Olive Mathieu Rouen Gabriella Barozzino‐Consiglio Amel BenAbdeladhim Jacques Maddaluno Anne Harrison‐Marchand |
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Institution: | Pauline Chaumont‐Olive,Mathieu Rouen,Gabriella Barozzino‐Consiglio,Amel Ben Abdeladhim,Jacques Maddaluno,Anne Harrison‐Marchand |
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Abstract: | An enantioselective aryl transfer is promoted using chiral tricoordinated lithium amido aryl zincates that are easily accessible reagents and whose chiral appendage is simply recovered for reuse. The arylation reaction is run in good yields (60 % average on twenty substrates) and high enantiomeric excesses (95 % ee average). This occurs whatever the ortho, meta, or para substituent borne by the substrate and a complete chemoselectivity is observed with respect to the aldehyde function. Sensitive groups such as nitriles, esters, ketones, and enolisable substrates resist to the action of the ate reagent, warranting a large scope to this methodology. |
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Keywords: | Chirales Lithiumamidozinkat Enantioselektiver Aryltransfer Nukleophile 1 2-Arylierung (R)-Neobenodin (R)-Orphenadrin |
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