Sugar-based phosphite and phosphoroamidite ligands for the Cu-catalyzed asymmetric 1,4-addition to enones |
| |
Authors: | Eva Raluy Oscar Pmies Montserrat Diguez Stephane Rosset Alexander Alexakis |
| |
Institution: | aDepartament de Química Física i Inorgànica, Universitat Rovira i Virgili, C/Marcel·lí Domingo s/n, 43007 Tarragona, Spain;bUniversity of Geneva, Department of Organic Chemistry, 30, Quai Ernest Ansermet, 1211 Genève 4, Switzerland |
| |
Abstract: | A modular sugar-based phosphoroamidite L1–L5a–g and phosphite L6–L9a–g ligand library was tested in the asymmetric Cu-catalyzed 1,4-conjugate addition reactions of β-substituted (cyclic and linear) and β,β′-disubstituted (cyclic) enones. The selectivity depended strongly on the configuration of carbon atom C-3, the size of the sugar backbone ring, the flexibility of the ligand backbone, the substituents and configurations in the biaryl phosphoroamidite moieties a–g, the type of functional group attached to the ligand backbone and the substrate structure. Therefore, by carefully selecting the ligand parameters, enantioselectivities of up to 60% for cyclic substrates and 72% for linear ones were achieved. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|