Cu(I)-catalyzed asymmetric allylation of ketones and ketimines*
نویسندگان
چکیده
Chiral CuF-catalyzed asymmetric allylation of ketones and ketimines is described. Nucleophile activation via transmetallation (allylboronate to allylcopper), which is facilitated by a cocatalyst [La(OPr)3 or LiO iPr], is key for these reactions. A CuOTf–3KOtBu–DUPHOS complex is a comparably effective catalyst that reduces the required amount of chiral phosphines.
منابع مشابه
Diastereoselective allylation and crotylation of N-unsubstituted imines derived from ketones.
A wide variety of tertiary carbinamines are synthesized in high yields via diastereoselective allylation and crotylation of in situ generated N-unsubstituted ketimines.
متن کاملImidazolylpyridine-In(OTf)3 catalyzed enantioselective allylation of ketimines derived from isatins.
An enantioselective In(OTf)3-catalyzed allylation of ketimines derived from isatins in the presence of an imidazolylpyridine ligand is described. The reaction proceeded smoothly under mild conditions and resulted in 3-allyl 3-aminooxindoles with good yields and moderate to excellent enantioselectivities (up to 97% ee).
متن کاملZn-mediated asymmetric allylation of N-tert-butanesulfinyl ketimines: an efficient and practical access to chiral quaternary 3-aminooxindoles.
Room temperature zinc-mediated diastereoselective allylation or propargylation of isatin-derived N-tert-butanesulfinyl ketimines for synthesis of highly enantiomerically enriched tetrasubstituted 3-aminooxindoles is described.
متن کاملDiastereoselective indium-mediated allylation of N-tert-butanesulfinyl ketimines: easy access to asymmetric quaternary stereocenters bearing nitrogen atoms.
Indium-mediated allylation of N-tert-butanesulfinyl ketimines afforded in high yields and diastereoselectivities homoallylic amine derivatives with the nitrogen atom bonded to a quaternary stereocenter.
متن کاملHighly diastereoselective and enantiospecific allylation of ketones and imines using borinic esters: contiguous quaternary stereogenic centers.
3,3-Disubstituted allylic boronic esters are not sufficiently reactive to react with ketones and imines. However, they can be converted into the corresponding borinic esters by the sequential addition of nBuLi and TFAA. These reactive intermediates possess the perfect balance between reactivity and configurational stability. Their enhanced reactivity allows the highly selective allylation of bo...
متن کامل