A novel C-2-symmetric bisphosphane ligand with a chiral cyclopropane backbone: synthesis and application in the Rh(I)-catalyzed asymmetric 1,4-addition of arylboronic acids

作者：Gok Yasar; Noel Timothy; Van der Eycken Johan^*

来源：Tetrahedron: Asymmetry , 2010, 21(23): 2768-2774.

DOI：10.1016/j.tetasy.2010.10.027

The synthesis of a novel C-2-symmetric bisphosphane ligand was accomplished starting from trans(2R,3R)-bis(3',5'-diphenylphenyl)cyclopropane-1,1-dimethanol as a key intermediate. This ligand was tested in the asymmetric rhodium(I)-catalyzed 1,4-addition to cyclic enones. We also compared the new ligand with a similar phosphane ligand with a less bulky cyclopropane backbone. Good yields (up to 99%) and enantioselectivities (up to 89% ee) were observed. We demonstrated that the presence of a more bulky cyclopropane backbone resulted in a less effective ligand.

• 出版日期2010-12-8