title: Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics.
abstract: New compounds with carbohydrate-similar structure (carbohydrate mimetics) are presented in this article. Starting from enantiopure nitrones and lithiated TMSE-allene we prepared three 1,2-oxazine derivatives which underwent a highly stereoselective Lewis acid-induced rearrangement to give bicyclic products in good yield. Subsequent reductive transformations delivered a library of new poly(hydroxy)aminooxepane derivatives. The crucial final palladium-catalyzed hydrogenolysis of the 1,2-oxazine moiety was optimized resulting in a reasonably efficient approach to a series of new seven-membered carbohydrate mimetics.
authors.affiliation: Freie Universität Berlin, Institut für Chemie und Biochemie, Takustrasse 3, D-14195 Berlin, Germany.
authors.forename: Léa
authors.initials: L
authors.lastname: Bouché
authors.affiliation: Freie Universität Berlin, Institut für Chemie und Biochemie, Takustrasse 3, D-14195 Berlin, Germany.
authors.forename: Maja
authors.initials: M
authors.lastname: Kandziora
authors.affiliation: Freie Universität Berlin, Institut für Chemie und Biochemie, Takustrasse 3, D-14195 Berlin, Germany.
authors.forename: Hans-Ulrich
authors.initials: HU
authors.lastname: Reissig
keywords: 1,2-oxazines; Lewis acid-induced; aminooxepanes; carbohydrate mimetics; hydrogenolyses; lithiated allenes; nitrones; rearrangements; reductions