title: Cerium(IV) ammonium nitrate mediated 5-endo-dig cyclization of α-amino allenylphosphonates to spirodienones.
abstract: α-Amino allenylphosphonates were treated with cerium(iv) ammonium nitrate under various conditions to form spirodienones in good to excellent yields. The 5-endo-dig cyclization proceeds through the formation of a key iminium intermediate. A comprehensive study on the nature of the solvent used for this reaction was undertaken resulting in the formation of three types of spirodienone scaffolds.
authors: Méthodologie, Synthèse et Molécules Thérapeutiques, ICMMO, UMR CNRS 8182 Bât. 410, Université Paris-Sud, 15 rue Georges Clemenceau, 91405 Orsay Cedex, France. nicolas.rabasso@u-psud.fr.
authors: Pauline
authors: P
authors: Adler
authors: Antoine
authors: A
authors: Fadel
authors: Nicolas
authors: N
authors: Rabasso
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D002563:Cerium / Q000737:chemistry*; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009566:Nitrates / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000466:Alkadienes; D007659:Ketones; D009566:Nitrates; D063065:Organophosphonates; D013141:Spiro Compounds; C532772:cerium(IV) ammonium nitrate; D002563:Cerium