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Chiral Lithium Amido Aryl Zincates: Simple and Efficient Chemo- and Enantio-Selective Aryl Transfer Reagents

By Pauline Chaumont-Olive, Mathieu Rouen, Gabriella Barozzino-Consiglio, Amel Ben Abdeladhim, Jacques Maddaluno and Anne Harrison-Marchand

Abstract

International audienceAn 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

Topics: [CHIM.ORGA]Chemical Sciences/Organic chemistry
Publisher: 'Wiley'
Year: 2019
DOI identifier: 10.1002/anie.201813510
OAI identifier: oai:HAL:hal-02060072v1
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