ChemInform Abstract: Anion-Stoichiometry-Dependent Selectivity Enhancement in Ion-Paired Chiral Ligand-Palladium Complex Catalyzed Enantioselective Allylic Alkylation.

ChemInform ◽  
2016 ◽  
Vol 47 (35) ◽  
Author(s):  
Kohsuke Ohmatsu ◽  
Yoshiyuki Hara ◽  
Yuya Kusano ◽  
Takashi Ooi
Keyword(s):  
Palladium Complex ◽  
Allylic Alkylation ◽  
Chiral Ligand

Anion-Stoichiometry-Dependent Selectivity Enhancement in Ion-Paired Chiral Ligand–Palladium Complex Catalyzed Enantioselective Allylic Alkylation

Synlett ◽  
2016 ◽  
Vol 27 (07) ◽  
pp. 1047-1050 ◽  
Author(s):  
Takashi Ooi ◽  
Kohsuke Ohmatsu ◽  
Yoshiyuki Hara ◽  
Yuya Kusano
Keyword(s):  
Palladium Complex ◽  
Allylic Alkylation ◽  
Chiral Ligand

scholarly journals Palladium-Catalyzed Diastereo- and Enantioselective Allylic Alkylation of Oxazolones with 1,3-Dienes Under Base-Free Conditions

2020 ◽  
Author(s):  
Haijian Yang ◽  
Dong Xing
Keyword(s):  
Catalytic System ◽  
Allylic Alkylation ◽  
Chiral Ligand ◽  
Palladium Hydride ◽  
Carbon Centers ◽  
Tertiary Carbon ◽  
Palladium Catalyzed

<p>Herein, we report a highly diastereo- and enantioselective allylic alkylation of oxozolones with 1,3-dienes by palladium-hydride catalyst under base-free conditions. With DTBM-SEGPHOS as the chiral ligand, a series of enantioenriched oxazolones bearing tertiary carbon centers were synthesized from substituted 1,3-dienes via exclusive 1,2-addition with moderate to good diastereoselectivities and high enantioselectivities. When simple 1,3-butadiene was used as the allyl precursor under this base-free catalytic system, 1,4-addition products were obtained in good yields with high regioselectivities. </p>

Exploring the utility of a new chiral phosphoramidite P,N-ligand derived from (R)-BINOL and 7-azaindole in asymmetric catalysis

2009 ◽  
Vol 87 (1) ◽  
pp. 72-79 ◽  
Author(s):  
Dominik Wechsler ◽  
Mark Stradiotto
Keyword(s):  
Asymmetric Catalysis ◽  
Platinum Group Metal ◽  
Allylic Alkylation ◽  
Chiral Ligand ◽  
Chemical Transformations ◽  
Group Metal ◽  
Alkene Hydrogenation ◽  
Platinum Group

Lithiation of 7-azaindole, followed by quenching with [(R)-(1,1′-binaphthalene-2,2′-diyl)]chlorophosphite afforded the new chiral phosphoramidite 1 in 92% isolated yield. Treatment of 0.5 equiv. of [(COD)MCl]2 (M = Rh, Ir; COD = η4-1,5-cyclooctadiene) with 2 equiv. of 1 afforded the corresponding [(κ1-P,N-1)(κ2-P,N-1)MCl] complexes in 68% (2a, Rh) and 72% (2b, Ir) yield, while treatment of (PPh3)3RhCl with 1 equiv. of 1 afforded [(PPh3)(κ2-P,N-1)RhCl] (3) as an analytically pure solid in 74% isolated yield. In examining the reaction of 1 with a mixture of 0.5 equiv. of [(COD)RhCl]2 and 1 equiv. of AgBF4, an inseparable mixture of [(κ2-P,N-1)2Rh]+BF4– (4a) and [(COD)(κ2-P,N-1)Rh]+BF4– (5a) was generated. Under analogous conditions employing [(COD)IrCl]2, the complex [(COD)(κ2-P,N-1)Ir]+BF4– (5b) was obtained in 86% isolated yield. Treatment of 0.5 equiv. of [(η3-allyl)PdCl]2 with 1 afforded [(η3-allyl)(κ2-P,N-1)Pd]+Cl– (6) in 86% isolated yield. The application of 1 in platinum group metal-mediated asymmetric chemical transformations, including alkene hydrogenation and hydroboration, ketone hydrosilylation, and allylic alkylation, was examined.Key words: chiral, ligand, phosphoramidite, asymmetric catalysis.

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