Journal
SCIENCE CHINA-CHEMISTRY
Volume 64, Issue 1, Pages 34-40Publisher
SCIENCE PRESS
DOI: 10.1007/s11426-020-9854-3
Keywords
palladium catalysis; iridium catalysis; asymmetric synthesis; dipolar cycloaddition; polycyclic indoles
Categories
Funding
- National Natural Science Foundation of China [21901072]
- China Postdoctoral Science Foundation [2019T120310]
- Shanghai Sailing Program [18YF140560]
- Research Center of Analysis and Test of East China University of Science and Technology
Ask authors/readers for more resources
The development of efficient methods for synthesizing chiral polycyclic indoles is crucial for their wide applications in medicines, pesticides, and other functional molecules. The study revealed novel indolyl substituted metal-allyl zwitterionic intermediates that could participate in asymmetric cycloaddition reactions with high selectivities, leading to the synthesis of diverse chiral polycyclic indoles.
The development of novel synthons and efficient methods to synthesize chiral polycyclic indoles has been a hot topic in organic synthesis and medicinal chemistry owing to their broad applications in medicines, pesticides, and other functional molecules. Here, we disclosed novel indolyl substituted metal-allyl zwitterionic intermediates through the decarboxylation of conveniently available vinyl indoloxazolidones, which could be regarded as two types of dipolar species through the anionic delocalization. The palladium-pi-allyl species tended to serve as an all-carbon 1,3-dipole in the asymmetric [3+2] cycloaddition with electron-deficient alkenes, which furnished polysubstituted cyclopenta[b]indoles with high regio- and stereoselectivities. Meanwhile, the iridium-pi-allyl species was recognized as an aza-1,3-dipole in asymmetric [3+2] cycloaddition with in situ generated C1 ammonium enolates, affording pyrrolo[1,2-a]indoles with high diastereo- and enantioselectivities. In addition, the dipolar cycloadditions could be easily scaled-up and several synthetic transformations of the cycloadducts were demonstrated for the rapid synthesis of diverse chiral polycyclic indoles.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available