Cp*Rh<sup>III</sup>/Chiral Disulfonate/CuOAc Catalyst System for the Enantioselective Intramolecular Oxyamination of Alkenes
Jumpei Hirose, Takumi Wakikawa, Shun Satake, M. Kojima, Manabu Hatano, Kazuaki Ishihara, Tatsuhiko Yoshino, Shigeki Matsunaga
Abstract
The enantioselective intramolecular oxyamination of unsaturated alkoxyamines using a hybrid catalytic system consisting of Cp*RhIII/chiral disulfonate/CuOAc is described. Tetrahydrofuran derivatives with a tetrasubstituted chiral center were obtained under the optimized conditions in 91:9–97:3 er. The use of a sterically hindered chiral disulfonate and a Cu additive was essential for the high enantioselectivity.
Topics & Concepts
Enantioselective synthesisIntramolecular forceChemistrySteric effectsCatalysisTetrahydrofuranMedicinal chemistryStereochemistryOrganic chemistrySolventCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis