Synthesis of enantiomerically pure alpha-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines.

J. Blanchet (1) , M. Bonin (2) , L. Micouin (2) , H. P. Husson (2)

1 ICSN - Institut de Chimie des Substances Naturelles
2 SSMIP - Synthèse et structure de molécules d'interet pharmacologique

Various oxazolidines prepared in two steps from (R)-phenylglycinol react at 0 degrees C with dialkylalkynylalane-triethylamine complexes in the presence of trimethylaluminum in high yield and diastereoselectivity. Enantiomerically pure primary alpha-substituted propargylamines can be easily obtained in two steps after removal of ferrocenylmethyl protective group under smooth acidic conditions and oxidative cleavage of the chiral appendage.

Domaines: Chimie organique

J. Blanchet, M. Bonin, L. Micouin, H. P. Husson. Synthesis of enantiomerically pure alpha-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines.. Journal of Organic Chemistry, 2000, 65 (20), pp.6423-6. ⟨hal-00909874⟩