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Chiral Lithium Amido Aryl Zincates: Simple and Efficient Chemo‐ and Enantio‐Selective Aryl Transfer Reagents
Author(s) -
ChaumontOlive Pauline,
Rouen Mathieu,
BarozzinoConsiglio Gabriella,
Ben Abdeladhim Amel,
Maddaluno Jacques,
HarrisonMarchand Anne
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201813510
Subject(s) - aryl , reagent , chemoselectivity , chemistry , lithium (medication) , enantioselective synthesis , aldehyde , substrate (aquarium) , lithium amide , combinatorial chemistry , substituent , enantiomer , organic chemistry , catalysis , medicine , alkyl , oceanography , geology , endocrinology
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.