An enantioselective asymmetric 1,4-addition of diarylphosphines to linear alpha,beta,gamma,delta-unsaturated dienones was developed. A series of chiral PCP- and PCN-transition-metal (Pd, Pt and Ni) pincers, themselves prepared catalytically via asymmetric hydrophosphination, were sequentially screened to reveal the roles of backbone architecture and metal ion in catalyst design. The selected ester-functionalized PCP-palladium pincer afforded the chiral 1,4-phosphine adducts in excellent yields with up to >99% ee. The same catalyst when utilized for the hydrophosphination of an alpha,beta,gamma,delta-unsaturated malonate ester also revealed the critical role played by the ester functionality on the ligand backbone in dictating the enantioselectivity of the 1,6-adduct.
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Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Aydin, Juhanes
Conrad, Cathrin S.
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Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Conrad, Cathrin S.
Szabo, Kalman J.
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Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
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Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Aydin, Juhanes
Kumar, K. Senthil
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Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Kumar, K. Senthil
Sayah, Mahmoud J.
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Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Sayah, Mahmoud J.
Wallner, Olov A.
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Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Wallner, Olov A.
Szabo, Kalman J.
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Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
机构:
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Aydin, Juhanes
Conrad, Cathrin S.
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h-index: 0
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Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Conrad, Cathrin S.
Szabo, Kalman J.
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Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
机构:
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Aydin, Juhanes
Kumar, K. Senthil
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h-index: 0
机构:
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Kumar, K. Senthil
Sayah, Mahmoud J.
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h-index: 0
机构:
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Sayah, Mahmoud J.
Wallner, Olov A.
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h-index: 0
机构:
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
Wallner, Olov A.
Szabo, Kalman J.
论文数: 0引用数: 0
h-index: 0
机构:
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, SwedenStockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden