Antonio Regla - Academia.edu (original) (raw)

Papers by Antonio Regla

Phosphorylation of amines, alcohols, and sulfoximines are accomplished using molecular iodine as ... more Phosphorylation of amines, alcohols, and sulfoximines are accomplished using molecular iodine as a catalyst and H 2 O 2 as the sole oxidant under mild reaction conditions. This method provides an easy route for synthesizing a variety of phosphoramidates, phosphorus triesters and sulfoximine-derived phosphoramidates which are of biological importance. Phosphoramidates and phosphate esters are structural scaffolds that are present in a variety of biologically active molecules. 1 Apart from their presence in a variety of biologically active natural products, phosphoramidates are useful pharmaceuticals (e.g., anti-HIV pro-drugs, cancer therapeutics, etc.) 2 and used as ligands 3a in asymmetric synthesis and hydroaminoalkylation catalysis, 3b as flame retardants, 3c and for efficient ionization in mass spectro-metric applications. 3d Phosphorylation of amines provides an excellent protocol for the protection of amines, which are stable to Lewis acids and can be cleaved by dilute mineral acids. 4 Similarly, phosphate esters are an integral part of a variety of naturally occurring molecules, such as nucleic acids, proteins, carbohydrates, steroids, and coen-zymes, and are used as pro-drugs. 5 Phosphate esters such as benzyl phosphates are employed as coupling partners in SuzukiÀMiyaura cross-coupling reactions. 6 The utility of the phosphoryl group as a directing group for CÀC bond-forming reactions has been well established. 7 For these reasons, the syntheses of phosphoramidate/phosphate es-ters are of great importance. The conventional methods for (1) (a) Phillips, D. R.; Uramoto, M.; Isono, K.; McCloskey, J. A.

Phosphorylation of amines, alcohols, and sulfoximines are accomplished using molecular iodine as ... more Phosphorylation of amines, alcohols, and sulfoximines are accomplished using molecular iodine as a catalyst and H 2 O 2 as the sole oxidant under mild reaction conditions. This method provides an easy route for synthesizing a variety of phosphoramidates, phosphorus triesters and sulfoximine-derived phosphoramidates which are of biological importance. Phosphoramidates and phosphate esters are structural scaffolds that are present in a variety of biologically active molecules. 1 Apart from their presence in a variety of biologically active natural products, phosphoramidates are useful pharmaceuticals (e.g., anti-HIV pro-drugs, cancer therapeutics, etc.) 2 and used as ligands 3a in asymmetric synthesis and hydroaminoalkylation catalysis, 3b as flame retardants, 3c and for efficient ionization in mass spectro-metric applications. 3d Phosphorylation of amines provides an excellent protocol for the protection of amines, which are stable to Lewis acids and can be cleaved by dilute mineral acids. 4 Similarly, phosphate esters are an integral part of a variety of naturally occurring molecules, such as nucleic acids, proteins, carbohydrates, steroids, and coen-zymes, and are used as pro-drugs. 5 Phosphate esters such as benzyl phosphates are employed as coupling partners in SuzukiÀMiyaura cross-coupling reactions. 6 The utility of the phosphoryl group as a directing group for CÀC bond-forming reactions has been well established. 7 For these reasons, the syntheses of phosphoramidate/phosphate es-ters are of great importance. The conventional methods for (1) (a) Phillips, D. R.; Uramoto, M.; Isono, K.; McCloskey, J. A.