One-pot three-component synthesis of alpha-iminonitriles by IBX/TBAB-mediated oxidative Strecker reaction.

Patrice Fontaine , Angèle Chiaroni (1) , Géraldine Masson (1) , Jieping Zhu (1)

1 ICSN - Institut de Chimie des Substances Naturelles

The reaction of aldehydes, amines, and TMSCN in the presence of 2-iodoxybenzoic acid (IBX) and tetrabutylammonium bromide (TBAB) afforded alpha-iminonitriles in good to excellent yields under mild conditions. The presence of TBAB is essential for this transformation. The methodology was applied to a two-step synthesis of indolizidine via a microwave-assisted intramolecular cycloaddition of alpha-iminonitrile.

Domaines: Biologie cellulaire

Patrice Fontaine, Angèle Chiaroni, Géraldine Masson, Jieping Zhu. One-pot three-component synthesis of alpha-iminonitriles by IBX/TBAB-mediated oxidative Strecker reaction.. Organic Letters, 2008, 10 (8), pp.1509-12. ⟨10.1021/ol800199b⟩. ⟨hal-00294575⟩