| Title: | Asymmetric spiroacetalization catalysed by confined Bronsted acids |
| Address: | "Max-Planck-Institut fur Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mulheim an der Ruhr, Germany" |
| ISSN/ISBN: | 1476-4687 (Electronic) 0028-0836 (Linking) |
| Abstract: | "Acetals are molecular substructures that contain two oxygen-carbon single bonds at the same carbon atom, and are used in cells to construct carbohydrates and numerous other molecules. A distinctive subgroup are spiroacetals, acetals joining two rings, which occur in a broad range of biologically active compounds, including small insect pheromones and more complex macrocycles. Despite numerous methods for the catalytic asymmetric formation of other commonly occurring stereocentres, there are few approaches that exclusively target the chiral acetal centre and none for spiroacetals. Here we report the design and synthesis of confined Bronsted acids based on a C(2)-symmetric imidodiphosphoric acid motif, enabling a catalytic enantioselective spiroacetalization reaction. These rationally constructed Bronsted acids possess an extremely sterically demanding chiral microenvironment, with a single catalytically relevant and geometrically constrained bifunctional active site. Our catalyst design is expected to be of broad utility in catalytic asymmetric reactions involving small and structurally or functionally unbiased substrates" |
| Keywords: | "Acetals/*chemical synthesis/*chemistry Animals Biological Products/*chemical synthesis/*chemistry/pharmacology Catalysis Catalytic Domain Female Male Models, Molecular Molecular Conformation Phosphoric Acids/*chemistry Sex Attractants/chemical synthesis/c;" |
| Notes: | "MedlineCoric, Ilija List, Benjamin eng Research Support, Non-U.S. Gov't England 2012/03/17 Nature. 2012 Mar 14; 483(7389):315-9. doi: 10.1038/nature10932" |
