用手性配体(Rc,Sp)-WalPhos与铑形成的配合物为催化剂,在1.0 MPa的氢气压力、二氯甲烷溶剂中以及室温的反应条件下,对β-取代β,γ-不饱和膦酸酯底物进行不对称催化氢化,合成了具有β-手性中心的手性膦酸酯类化合物,所有考察的底物均可完全转化,最高获得了87%的ee值.
参考文献
[1] | Hilderbrand R L.The Role of Phosphonates in Living Systems[M].CRC Press,Boca Raton,1983. |
[2] | Bellucci C,Gualtieri F,Scapecchi S,et al.Negative Inotropic and Calcium-antagonist Activity of Alkil and Arylalkyl Phosphonates[J].Ⅱ Farmaco,1989,44:1167-1191. |
[3] | Kafarski P,Lejczak B.Biological Activity of Aminophosphonic Acids[J].Phosphorus Sulfur Silicon Relat Elem,1991,63:193-215. |
[4] | Savignac P,Iorga B.Morden Phosphonate Chemistry[M].CRC Press,Boca Raton,2003. |
[5] | Hayashi T,Senda T,Takaya Y,et al.Rhodium-Catalyzed Asymmetric 1,4-Addition to 1-Alkenylphosphonates[J].J Am Chem Soc,1999,121:11591-11592. |
[6] | Duan Z C,Hu X P,Wang D Y,et al.Cu-Catalyzed Asymmetric Conjugate Reduction of β-Substituted α,β-Unsaturated Phosphonates:an Efficient Synthesis of Optically Active β-Stereogenic Alkylphosphonates[J].Tetrahedron Lett,2009,50:6720-6722. |
[7] | de Vries J G.The Handbook of Homogeneous Hydrogenation[M].Wiley-VCH:Weinheim,Germany,2007:1-3. |
[8] | Duan Z C,Hu X P,Wang D Y,et al.Enantioselective Synthesis of Optically Active Alkanephosphonates via RhodiumCatalyzed Asymmetric Hydrogenation of beta-Substituted alpha,beta-Unsaturated Phosphonates with Ferrocene-based Monophosphoramidite Ligands[J].Adv Synth Catal,2008,350:1979-1983. |
[9] | Duan Z C,Hu X P,Zhang C,et al.Highly Enantioselective Rh-Catalyzed Hydrogenation ofβ,γ-Unsaturated Phosphonates with Chiral Ferrocene-Based Monophosphoramidite Ligands[J].J Org Chem,2009,74:9191-9194. |
[10] | Luo L B,Wang D Y,Zhou X M,et al.Asymmetric Synthesis of 2-Alkyl-3-Phosphonopropanoic Acid Derivatives via RhCatalyzed Asymmetric Hydrogenation[J].Tetrahedron:Asymm,2011,22:2117-2123. |
[11] | Duan Z C,Wang L Z,Song X J,et al.Enantioselective Synthesis of Optically Active Alkylphosphonates via Rh-Catalyzed Asymmetric Hydrogenation of β-Substituted α,β-Unsaturated Phosphonates[J].Tetrahedron:Asymm,2012,23:508-514. |
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