Asymmetric Alkynylation of β-Ketoesters and Naphthols Promoted by New Chiral Biphenylic Iodanes

S. Companys , P.A. Peixoto , C. Bosset , Stefan Chassaing , Karinne Miqueu (1) , Jean-Marc Sotiropoulos (1) , L. Pouységu , S. Quideau

1 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux

The preparation of new chiral biphenylic λ3-iodane reagents bearing transferable alkynyl ligands is described. These reagents transfer their carbon-based ligands onto β-ketoesters with an enantiomeric excess (ee) up to 68 %, and most remarkably, enable the dearomative alkynylation of naphthols in good to high yields up to 84 % ee. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Mots clés: alkynylation; asymmetric synthesis; hypervalent compounds; iodanes; metal-free reactions

Domaines: Chimie

S. Companys, P.A. Peixoto, C. Bosset, Stefan Chassaing, Karinne Miqueu, et al.. Asymmetric Alkynylation of β-Ketoesters and Naphthols Promoted by New Chiral Biphenylic Iodanes. Chemistry - A European Journal, 2017, 23 (54), pp.13309--13313. ⟨10.1002/chem.201703238⟩. ⟨hal-01617281⟩