Catalytic Enantioselective Conjugate Alkynylation of α,β-Unsaturated 1,1,1-Trifluoromethyl Ketones with Terminal Alkynes
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Sanz-Marco, Amparo
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Blay, Gonzalo
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Univ Valencia, Fac Quim, Dept Quim Organ, C Dr Moliner 50, Burjasso 46100, SpainUniv Valencia, Fac Quim, Dept Quim Organ, C Dr Moliner 50, Burjasso 46100, Spain
Blay, Gonzalo
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Carmen Munoz, M.
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Univ Politecn Valencia, Dept Fis Aplicada, Cami Vera S-N, E-46022 Valencia, SpainUniv Valencia, Fac Quim, Dept Quim Organ, C Dr Moliner 50, Burjasso 46100, Spain
Carmen Munoz, M.
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Pedro, Jose R.
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[1] Univ Valencia, Fac Quim, Dept Quim Organ, C Dr Moliner 50, Burjasso 46100, Spain
[2] Univ Politecn Valencia, Dept Fis Aplicada, Cami Vera S-N, E-46022 Valencia, Spain
The first catalytic enantioselective conjugate alkynylation of alpha,beta-unsaturated 1,1,1-trifluoromethyl ketones has been carried out. Terminal alkynes and 1,3-diynes were treated with trifluoromethyl ketones in the presence of a low catalytic load of a Cu-I-MeOBIPHEP complex (2.5 mol%) and triethylamine (10 mol%) to give the corresponding trifluoromethyl ketones bearing a propargylic stereogenic center at the beta position with good yields and excellent enantiomeric excesses in most of the cases. No 1,2-addition products were formed under the reaction conditions. The procedure showed broad substrate scope for alkyne, diyne, and enone. A rationale for the observed stereochemistry has been provided. Finally, the potential application of the reaction products in the synthesis of chiral tetrahydrofurans bearing a trifluoromethylated quaternary stereocenter has been devised.
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Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R ChinaTianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
Zhang, Guang-Wu
Meng, Wei
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Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R ChinaTianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
Meng, Wei
Ma, Hai
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Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R ChinaTianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
Ma, Hai
Nie, Jing
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Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R ChinaTianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
Nie, Jing
Zhang, Wen-Qin
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Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R ChinaTianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
Zhang, Wen-Qin
Ma, Jun-An
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Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R ChinaTianjin Univ, Dept Chem, Tianjin 300072, Peoples R China