Article When Phosphosugars Meet Gold: Synthesis and Catalytic Activities of Phostones and Polyhydroxylated Phosphonite Au(I) Complexes Gaëlle Malik, Angélique Ferry and Xavier Guinchard * Received: 23 September 2015 ; Accepted: 20 November 2015 ; Published: 27 November 2015 Academic Editor: Bimal Banik Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif sur Yvette cedex, France;
[email protected] (G.M.);
[email protected] (A.F.) * Correspondence:
[email protected]; Tel.: +33-1-69-82-30-66 Abstract: The synthesis and characterization of P-chiral phosphonite-, phosphonate- and thiophosphonate-Au(I) complexes are reported. These novel ligands for Au(I) are based on glycomimetic phosphorus scaffolds, obtained from the chiral pool. The catalytic activities of these complexes are shown in the cyclization of allenols and the hydroamination of 2-(2-propynyl)aniline combined with an organocatalyzed reduction to the corresponding 2-phenyl tetrahydroquinoline. All described gold complexes present excellent catalytic activities. Keywords: gold catalysis; phosphosugars; catalysis; heterocycles; P-stereogeny 1. Introduction One of the major advances of the 21th century in organic chemistry is undoubtedly the increased importance of gold catalysis. Long believed to be useless for catalysis, gold complexes have emerged as powerful tools for the catalysis of myriads of reactions [1–9]. In particular, the gold tolerance towards air, moisture and numerous chemical functionalities renders the use of these catalysts very convenient. However, the bicoordinate linear geometry of gold(I) complexes makes the control of the asymmetry difficult, the chiral ligand being placed in a distal position to the reactive cationic center.