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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Preparation of spiro[4.4]oxaphospholene and -azaphospholene systems from carbohydrate templates
Marina Moura1, Solen Josse, Denis Postel
1Laboratoire des Glucides, CNRS-FRE 3517 , 10 rue Baudelocque, 80039 Amiens, France.
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.
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