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新型手性P,N配体的开发及其在铜催化二乙基锌对烯酮的对映选择性共轭加成反应中的应用

Development of New Chiral P,N Ligands and Their Application in the Cu-Catalyzed Enantioselective Conjugate Addition of Diethylzinc to Enones.

作者信息

Hu X, Chen H, Zhang X

机构信息

Department of Chemistry, The Pennsylvania State University, University Park, PA 16802 (USA).

出版信息

Angew Chem Int Ed Engl. 1999 Dec 3;38(23):3518-3521. doi: 10.1002/(sici)1521-3773(19991203)38:23<3518::aid-anie3518>3.0.co;2-p.

DOI:10.1002/(sici)1521-3773(19991203)38:23<3518::aid-anie3518>3.0.co;2-p
PMID:10602227
Abstract

High enantioselectivity (up to 98 % ee) has been achieved for the conjugate addition of diethylzinc to acyclic enones utilizing Cu(I) complexes of the novel chiral P,N ligands 1. The high enantioselectivities are best achieved using Cu(OTf) small middle dotC(6)H(6) as the copper catalyst precursor in nonpolar solvents such as toluene or Cl(CH(2))(2)Cl. R=H, CH(3); Tf=F(3)CSO(2).

摘要

利用新型手性P,N配体1的Cu(I)配合物,实现了二乙基锌与开链烯酮的共轭加成反应的高对映选择性(高达98%ee)。使用[Cu(OTf)]₂·C₆H₆作为铜催化剂前体,在甲苯或Cl(CH₂)₂Cl等非极性溶剂中能最好地实现高对映选择性。R = H,CH₃;Tf = F₃CSO₂ 。

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