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.

DOI: 10.1021/jo400954p

Cite this paper

@article{Moura2013PreparationOS, title={Preparation of spiro[4.4]oxaphospholene and -azaphospholene systems from carbohydrate templates.}, author={Marina P Moura and Solen Josse and Denis Postel}, journal={The Journal of organic chemistry}, year={2013}, volume={78 18}, pages={8994-9003} }