Enantioselective Copper??Catalysed Propargylic Substitution: Synthetic Scope Study and Application in Formal Total Syntheses of (+)??Anisomycin and (−)??Cytoxazone

…, H Hiemstra, JH van Maarseveen

Index: Detz, Remko J.; Abiri, Zohar; Le Griel, Remi; Hiemstra, Henk; Van Maarseveen, Jan H. Chemistry - A European Journal, 2011 , vol. 17, # 21 p. 5921 - 5930

Full Text: HTML

Citation Number: 55

Abstract

Abstract 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, ...