2002
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Abstract: Readily available chiral phosphoramidites are a promising class of ligands for nickel-catalyzed asymmetric hydrovinylation of vinyl arenes. Cooperative effects are operative when ligands with more than one element of chirality are used. Choosing the proper stereochemistry in each part of the modular ligand system leads to high chemoselectivities and excellent enantioselectivities up to 94%. Moreover, the catalysts derived from these ligands proved extremely efficient and remarkably robust performing up to 8300… Show more

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“…Next, effect of different solvents on the selectivities was examined. The reactions in toluene, tetrahydrofuran, CH 2 Cl 2 , and MeOH also gave 8 in complete conversion under the same reaction conditions and no hydrogenation product was observed (entries [11][12][13][14]. However, the reactions in tetrahydrofuran and CH 2 Cl 2 gave 8 with lower branched-to-linear ratio and enantiopurity (entries 12 and 13), and the reaction in MeOH gave lower enantioselectivity (entry 14) than those in benzene and toluene.…”
Section: Resultsmentioning
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“…Next, effect of different solvents on the selectivities was examined. The reactions in toluene, tetrahydrofuran, CH 2 Cl 2 , and MeOH also gave 8 in complete conversion under the same reaction conditions and no hydrogenation product was observed (entries [11][12][13][14]. However, the reactions in tetrahydrofuran and CH 2 Cl 2 gave 8 with lower branched-to-linear ratio and enantiopurity (entries 12 and 13), and the reaction in MeOH gave lower enantioselectivity (entry 14) than those in benzene and toluene.…”
Section: Resultsmentioning
“…1). These ligands have found a wide range of applications in metalcatalyzed asymmetric transformations such as hydrogenation (5,(8)(9)(10)), 1,4-additions of dialkylzinc (11,12) and boronic acids (13) to enones, hydrovinylation (14), hydrosilylation (15), intramolecular Heck reaction (16), hydroformylation (17), allylic alkylation (18,19), amination (20), and etherification (21).…”
mentioning
“…Phosphoramidites have been successfully employed in the copper-catalysed asymmetric diethylzinc addition to enones, [16] iridium-catalysed substitution of allylic acetates, [17] copper-catalysed allylic alkylations, [18] rhodium-catalysed asymmetric olefin hydrogenations, [19] palladium-catalysed asymmetric Heck reactions, [20] rhodium-catalysed asymmetric arylation of enones, [21] nickel-catalysed asymmetric hydrovinylations, [22] and palladium-catalysed asymmetric hydrosilylation of olefins. [23] The use of MonoPhos TM (7a) in the hydroformylation of allyl cyanide gave good results with respect to chemo-and regioselectivity.…”
Section: Resultsmentioning
“…[38] More recently, it has been shown that monodentate phosphoramidites can function as effective chiral ligands in other metal-catalysed reactions such as hydrogenations, [39,40] hydrosilylations [41] and hydrovinylations. [42] Despite the recent increase in interest for phosphoramidites as auxiliaries in catalysis, very few applications in palladium-catalysed allylic subtitution have been reported yet. [43] Several groups have exemplified the potential of chiral phosphoramidites in copper-catalysed allylic alkylations, which proceed through a mechanism (predominantly S N 2' from s-allyl complexes) different from that of the palladium-catalysed reaction.…”
Section: Introductionmentioning