An enantioselective synthesis of 3-aryl-4-phosphonobutyric acid esters via Cu-catalyzed asymmetric conjugate reduction

作者：Guo, Wei-Lei; Hou, Chuan-Jin^*; Duan, Zheng-Chao; Hu, Xiang-Ping

来源：Tetrahedron: Asymmetry , 2011, 22(24): 2161-2164.

DOI：10.1016/j.tetasy.2011.12.009

• DYNAMIC KINETIC-RESOLUTION
• BOPHOZ-TYPE LIGAND
• ALPHA,BETA-UNSATURATED ESTERS
• DIASTEREOSELECTIVE SYNTHESIS
• HYDROGENATION
• PHOSPHONATES
• DERIVATIVES
• INHIBITORS
• HYDROXYPHOSPHONATES
• HYDROSILYLATIONS

The asymmetric conjugate reduction of 3-aryl-4-phosphonobutenoates has been demonstrated which provides an enantioselective synthesis of optically active 3-aryl-4-phosphonobutyric acid esters. A wide range of 3-aryl-4-phosphonobutenoate derivates are reduced with high enantioselectivities (up to 94% ee) using an (S)-Segphos/Cu(OAc)(2)center dot H2O catalyst system (1 or 5 mol %) in the presence of PMHS and t-BuOH. The reduction is influenced by the steric and electronic effects of the substrates.

• 出版日期2011-12-31
• 单位大连工业大学; 中国科学院大连化学物理研究所