Organic Letters · 2023 · 15 citations · 45 references
PharmacyChemistryMedicinal ChemistryDrug DesignDrug DiscoverySynthetic Medicinal ChemistryDiversity-oriented SynthesisHigh-throughput SynthesisTarget-oriented SynthesisAmide Bond FormationChemoselective Library SynthesisFunctional Group ToleranceLate-stage DiversificationOrganic Molecule SynthesisOrganozinc CompoundsOrganozinc CouplingOrganozinc Synthesis
High Resolution Image Download MS PowerPoint Slide Herein, we present a novel C(sp 3 )–C(sp 3 ) bond-forming protocol via the reductive coupling of abundant tertiary amides with organozinc reagents prepared in situ from their corresponding alkyl halides. Using a multistep fully automated flow protocol, this reaction could be used for both library synthesis and target molecule synthesis on the gram-scale starting from bench-stable reagents. Additionally, excellent chemoselectivity and functional group tolerance make it ideal for late-stage diversification of druglike molecules.
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Copper-mediated synthesis of drug-like bicyclopentanes
Xiaheng Zhang, Russell T. Smith, Stefan J. McCarver et al. · Nature · 2020 · 347 citations · Full text
Joel M. Smith, Stephen J. Harwood, Phil S. Baran · Accounts of Chemical Research · 2018 · 297 citations