605662-85-9Relevant articles and documents
Enantioselective copper-catalysed propargylic substitution: Synthetic scope study and application in formal total syntheses of (+)-anisomycin and (-)-cytoxazone
Detz, Remko J.,Abiri, Zohar,Le Griel, Remi,Hiemstra, Henk,Van Maarseveen, Jan H.
experimental part, p. 5921 - 5930 (2011/06/26)
A copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic esters with different side chains (R=Ar, Bn, alkyl) into their amine counterparts in very high yields and with good enantioselectivities (up to 90% enantiomeric excess (ee)). Different amine nucleophiles were applied in the reactions and the highest enantioselectivities were obtained for aniline and its analogues. Interestingly, some carbon nucleophiles could also be used and with indoles excellent ee values were obtained (up to 98% ee). The versatility of the propargylic amines obtained was demonstrated by their further elaboration to formal total syntheses of the antibiotic (+)-anisomycin and the cytokine modulator (-)-cytoxazone. Copyright
Enantioselective synthesis of propargylamines through Zr-catalyzed addition of mixed alkynylzinc reagents to arylimines
Traverse, John F.,Hoveyda, Amir H.,Snapper, Marc L.
, p. 3273 - 3275 (2007/10/03)
(Matrix presented) Addition of mixed alkynylzinc reagents to various arylimines is catalyzed by chiral amino acid-based ligand 1 and Zr(Oi-Pr) 4·HOi-Pr to afford chiral propargylamines in up to 90% ee. Oxidative removal of the o-anisidyl group
