120349-79-3Relevant academic research and scientific papers
Palladium-catalyzed, asymmetric Mizoroki-Heck reaction of benzylic electrophiles using phosphoramidites as chiral ligands
Yang, Zhigang,Zhou, Jianrong
supporting information; experimental part, p. 11833 - 11835 (2012/09/08)
We report herein the first examples of asymmetric Mizoroki-Heck reactions using benzyl electrophiles. A new phosphoramidite was identified to be an effective chiral ligand in the palladium-catalyzed reaction. The reaction is compatible with polar functional groups and can be readily scaled up. Several cyclic olefins worked well as olefin components. Thirty-one examples are included.
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.
, 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
