A rhodium catalyzed cycloisomerization and tandem Diels-Alder reaction for facile access to diverse bicyclic and tricyclic heterocycles.
Yirong ZhouAli NikbakhtFelix BauerBernhard BreitPublished in: Chemical science (2019)
A regioselective distal cycloisomerization of 1,6-allenenes was successfully developed to afford six-membered ring exocyclic 1,3-dienes employing a rhodium/diphosphine catalyst system. Deuterium labelling experiments and DFT calculations were performed to provide insights into the reaction mechanism of this unprecedented transformation. In addition, one-pot tandem Diels-Alder reactions with various dienophiles could readily construct diverse bicyclic and tricyclic nitrogen heterocycles, which are ubiquitous core scaffolds for a variety of natural products and bioactives. High efficiency and exclusive chemo and regioselectivities for a broad substrate scope were achieved under mild conditions using a low catalyst loading of 0.5 mol%.
Keyphrases
- high efficiency
- room temperature
- reduced graphene oxide
- highly efficient
- density functional theory
- metal organic framework
- visible light
- ionic liquid
- carbon dioxide
- gold nanoparticles
- photodynamic therapy
- molecular dynamics
- molecular dynamics simulations
- minimally invasive
- cancer therapy
- molecular docking
- tissue engineering
- quantum dots
- electron transfer
- combination therapy
- radiation therapy
- structural basis
- monte carlo