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

Simon Companys; Philippe A Peixoto; Cyril Bosset; Stefan Chassaing; Karinne Miqueu; Jean-Marc Sotiropoulos; Laurent Pouységu; Stéphane Quideau

doi:10.1002/chem.201703238

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

Chemistry. 2017 Sep 27;23(54):13309-13313. doi: 10.1002/chem.201703238. Epub 2017 Aug 21.

Authors

Simon Companys¹, Philippe A Peixoto¹, Cyril Bosset¹, Stefan Chassaing², Karinne Miqueu³, Jean-Marc Sotiropoulos³, Laurent Pouységu¹, Stéphane Quideau¹

Affiliations

¹ Univ. Bordeaux, ISM (CNRS-UMR 5255), 351 cours de la Libération, 3, 3405, Talence Cedex, France.
² ITAV, Univ. Toulouse, CNRS, UPS, 31106, Toulouse, France.
³ Univ. Pau et Pays de l'Adour, IPREM (CNRS-UMR 5254), Hélioparc, 2 avenue Pierre Angot, 64053, Pau Cedex 09, France.

PMID: 28715080
DOI: 10.1002/chem.201703238

Abstract

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.

Keywords: alkynylation; asymmetric synthesis; hypervalent compounds; iodanes; metal-free reactions.