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Relevant academic research and scientific papers

Enantioselective conjugate addition of dialkylzincs to α,β- unsaturated enones catalyzed by Ni(acac)2 and (+)-(1S,2R)-7,7- dimethyl-1-morpholinoisonorborneol

A mixture of chiral ligand 4 [(+)-MINBOL] and Ni(acac)2 (12.5 and 0.5 mol % respectively) is able to successfully catalyze the enantioselective conjugate 1,4-addition of dialkylzinc to α,β- unsaturated enones in propionitrile to give the corres

Multinuclear Cu-catalysts based on SPINOL-PHOS in asymmetric conjugate addition of organozinc reagents

Multinuclear Cu/Zn complex-catalyzed efficient asymmetric conjugate addition of organozinc reagents to acyclic and cyclic enones has been developed in the presence of a wide variety of regioisomeric chiral diols bearing phosphorus moieties as ligands. The

Binaphthol-catalyzed asymmetric conjugate arylboration of enones

Conjugate addition of arylboronates to α,β-unsaturated ketones may be catalyzed by chiral binaphthols with enantioselectivities of up to 99:1. Best results were observed with 3,3′-dichloro-BINOL. This chemistry was applied to syntheses of intermediates fo

Multinuclear catalyst for copper-catalyzed asymmetric conjugate addition of organozinc reagents

(Figure Presented) A whole lot o' metal: An efficient copper-catalyzed asymmetric conjugate addition was achieved using a binol-derived ligand. The catalytic system has a turnover number of 2000, and the excellent cata-lytic performance could be attributed to the generation of a multinuclear complex such as 1. binol = 2, 2'-dihydroxy-l, 1'-binaphthyl.

Remarkable effect of silyl groups on asymmetric induction in a conjugate addition reaction with O-methylnorephedrine-based N-silylamidocuprates

Scalemic N-silylamidocuprates, prepared from O-methylnorephedrine in a two-flask procedure, are exceedingly reactive and give excellent enantiomeric excesses with chalcone, a classic substrate for studies of organocuprate conjugate addition. For example, the butyl N-diphenylmethylsilylamidocuprate (T = Bu) affords a 99.2% ee (99% yield) of (S)-3-butyl-1,3-diphenyl-1-propanone. The remarkably high yields with this and other silyl ligands are attributed to the extraordinary activating effect of a β-silicon atom on organocuprate reactions. The high ee is a consequence of the larger size of the silyl ligands compared to that of the unsubstituted or methyl-substituted analogues. Copyright

Chiral bicyclic phosphoramidites - A new class of ligands for asymmetric catalysis

The development of new ligands for catalytic asymmetric C-C bond formation is of great interest to organic synthesis. We describe here a new class of chiral phosphoramidites that embody one or two binaphthol units attached to an achiral azabicyclic [3.3.1] or [3.3.0] framework. These ligands were easily accessible from (R)-1,1′-binaphthyl-2,2′-dioxaphosphorchloridite (4) and the corresponding heterobicyclic core 1, 2, or 3. They were employed in enantioselective Cu-catalyzed additions of different dialkylzinc reagents to cyclic and acyclic enones. The chiral ketones were obtained with an enantiomeric ratio up to 91:9. The choice of the best ligand proved to be strongly dependent on each substrate. In addition, ligand 6 was found to be the most suitable for Rh-catalyzed hydrogenations of α,β-unsaturated esters, giving rise to dimethyl 2-methylsuccinate and methyl N-acetylalaninate with enantiomer ratios up to 95:5.

Chiral Homoenolate Equivalents, III Asymmetric Synthesis of 3-Substituted 3-Phenylketones via Metallated SMP-Allylamines

The diastereomeric excess obtained in alkylation reactions of the chiral homoenolate equivalents 7 with prolinol ether as chiral auxiliary leading to the formation of 3-phenylketones 9 clearly depends on the temperature, the counter ion and the size of the alkyl iodide.But most important is the influence of the solvent used.By its variation even the course of induction may be controlled.Normally, the selectivity amounts to about 8:1 only.The best results (about 9:1) are obtained with lithium as counter ion and tert-butyl methyl ether as solvent.

Asymmetric Synthesis of Optically Active β-Substituted Ketones by Highly Enantioselective Catalytic Conjugate Addition of Dialkylzinc Reagents to Enones using a Catalyst System of Nickel(II)-Chiral Ligand-Achiral Ligand in Acetonitrile/Toluene

Highly enantioselective conjugate addition of dialkylzinc reagents to aryl substituted enones using Ni(II)-bipyridyl-chiral ligand in acetonitrile (MeCN)/toluene as an in situ prepared catalyst system affords β-substituted ketones in up to 90percent enant