Auberger N, Onfroy B, Fontelle N, Foucart Q, Blériot Y
Equipe Synthèse Organique - Groupe Glycochimie Institut de Chimie des Milieux et Materiaux de Poitiers (IC2MP), UMR-CNRS 7285, Université de Poitiers, Bâtiment B28, TSA 51106, 4 rue Michel Brunet, 86073, Poitiers cedex 9, France.
Equipe Synthèse Organique - Groupe Glycochimie Institut de Chimie des Milieux et Materiaux de Poitiers (IC2MP), UMR-CNRS 7285, Université de Poitiers, Bâtiment B28, TSA 51106, 4 rue Michel Brunet, 86073, Poitiers cedex 9, France.
Carbohydr Res. 2019 Jan 15;472:65-71. doi: 10.1016/j.carres.2018.11.008. Epub 2018 Nov 13.
The Lewis acid-catalyzed nucleophilic opening of a D-gluco-configured bicyclic hemiaminal has been examined. Several Lewis acids and silylated nucleophiles have been screened allowing the introduction of acetophenone, phosphonate or nitrile at the pseudoanomeric position in satisfactory yields and high 1,2 trans stereoselectivities. Their skeletal rearrangement triggered by the N-benzyl anchimeric assistance provided the corresponding L-ido-configured piperidines displaying various functional groups at C-6 position in good yield.
对D-葡萄糖构型的双环半缩醛胺在路易斯酸催化下的亲核开环反应进行了研究。筛选了几种路易斯酸和硅烷化亲核试剂，能够以令人满意的产率和高的1,2-反式立体选择性在假端基异构位置引入苯乙酮、膦酸酯或腈。由N-苄基邻基参与辅助引发的骨架重排以良好的产率提供了相应的L-艾杜糖构型的哌啶，其在C-6位带有各种官能团。
