Synthesis of enantiomerically pure alpha-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines.
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.
Blanchet
J
J
Laboratoire de Chimie Thérapeutique UMR 8638, l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques 4, Paris, France.
Bonin
M
M
Micouin
L
L
Husson
H P
HP
D000114:Acetylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000535:Aluminum; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009942:Organometallic Compounds / Q000737:chemistry*; D023303:Oxazolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D009942:Organometallic Compounds; D023303:Oxazolidinones; D000535:Aluminum; D000114:Acetylene