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Synthesis of enantiomerically pure alpha-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines. 2000
Laboratoire de Chimie Thérapeutique UMR 8638, l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques 4, Paris, France.
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.
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