Reactivity of sugar α-aminonitrile derivatives under titanium-mediated cyclopropanation conditions

Delphine Declerck (1) , Solen Josse (1) , Albert Nguyen van Nhien (1) , Jan Szymoniak (2) , Philippe Bertus (3) , Denis Postel (1)

1 LG - Laboratoire des Glucides
2 ICMR - Institut de Chimie Moléculaire de Reims - UMR 7312
3 UCO2M - Unité de chimie organique moléculaire et macromoléculaire

The reactivity of different sugar α-aminonitriles has been studied under titanium-mediated cyclopropanation conditions. This study has been performed on amide, lactam, and imide derivatives. It has been possible to obtain spiro[furanose-3,3′-(3′,5′,6′,7′-tetrahydrospiro[cyclopropane-1,2′-pyrrolo[1,2-a]imidazole])] derivatives.

Mots clés: Nitriles; Cyclopropylamine; Titanium-catalyzed cyclopropanation; Imidazoline

Domaines: Chimie organique

Delphine Declerck, Solen Josse, Albert Nguyen van Nhien, Jan Szymoniak, Philippe Bertus, et al.. Reactivity of sugar α-aminonitrile derivatives under titanium-mediated cyclopropanation conditions. Tetrahedron, 2012, 68 (4), pp.1145-1152. ⟨10.1016/j.tet.2011.11.067⟩. ⟨hal-00711787⟩