title: Preparation of spiro[4.4]oxaphospholene and -azaphospholene systems from carbohydrate templates.
abstract: Introduction of a spiro-phosphorus cycle in position 3 of monosaccharidic derivatives was studied starting from cyanohydrin or aminonitrile A. A two-step procedure involving (i) phosphonylation and (ii) carbanion-mediated phosphonate intramolecular cyclization (denoted CPIC) was used. The necessity of having an electron-withdrawing group α to the phosphorus atom in order to avoid undesired reactions was demonstrated.
authors: Laboratoire des Glucides, CNRS-FRE 3517 , 10 rue Baudelocque, 80039 Amiens, France.
authors: Marina
authors: M
authors: Moura
authors: Solen
authors: S
authors: Josse
authors: Denis
authors: D
authors: Postel
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001372:Aza Compounds; D002241:Carbohydrates; D009943:Organophosphorus Compounds; D013141:Spiro Compounds; C586598:spiro(4.4)oxaphospholene