Bimetallic Rhodium(II)/Indium(III) Relay Catalysis for Tandem Insertion/Asymmetric Claisen Rearrangement.
Yushuang ChenShunxi DongXi XuXiao-Hua LiuXiaoming FengPublished in: Angewandte Chemie (International ed. in English) (2018)
The first example of catalytic insertion/asymmetric Claisen rearrangement tandem reaction of N-sulfonyl-1,2,3-triazoles with allyl alcohol esters was achieved by bimetallic relay catalytic systems involving achiral rhodium salt and chiral N,N'-dioxide-indium(III) complex. This manifold could overcome the limitation of single RhII catalysis, providing a straight and facile route to various enantioenriched β/γ-amino acid derivatives in high yields (up to 99 %) with excellent diastereo- and enantioselectivities (up to >95:5 dr, 98:2 er). Moreover, possible transition state models were proposed to elucidate the origin of chiral induction based on the control experiments and X-ray crystal structure of the catalyst.
Keyphrases
- metal organic framework
- visible light
- ionic liquid
- amino acid
- capillary electrophoresis
- reduced graphene oxide
- highly efficient
- high resolution
- solid state
- crystal structure
- room temperature
- breast cancer cells
- editorial comment
- mass spectrometry
- alcohol consumption
- endoplasmic reticulum
- quantum dots
- estrogen receptor
- gold nanoparticles
- computed tomography
- magnetic resonance imaging
- structure activity relationship