Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents

Sébastien Alazet; Franck Le Vaillant; Stefano Nicolai; Thibaut Courant; Jerome Waser

doi:10.1002/chem.201702599

Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents

Chemistry. 2017 Jul 18;23(40):9501-9504. doi: 10.1002/chem.201702599. Epub 2017 Jun 27.

Authors

Sébastien Alazet¹, Franck Le Vaillant¹, Stefano Nicolai¹, Thibaut Courant^{1

2}, Jerome Waser¹

Affiliations

¹ Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015, Lausanne, Switzerland.
² Current address: Laboratoire COBRA-Bâtiment IRCOF UMR 6014, CNRS-INSA, Université de Rouen 1, Rue Tesnière, 76281, Mont-Saint-Aignan Cedex, France.

PMID: 28605075
DOI: 10.1002/chem.201702599

Abstract

A versatile synthesis of azidolactones through azidation and cyclization of carboxylic acids onto alkenes has been developed. Based on either photoredox or palladium catalysis, (1,1) and (1,2) azido lactones can be selectively synthesized. The choice of catalyst and benziodoxol(on)e reagent serving as azide source was essential to initiate either a radical or Lewis acid mediated process with divergent outcome. These transformations were carried out under mild conditions using a low catalyst loading and gave access to a large scope of azido lactones.

Keywords: 1,2 shift; azides; hypervalent iodine; lactones; photoredox.