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Catalytic asymmetric dipolar cycloadditions of indolyl delocalized metal-allyl species for the enantioselective synthesis of cyclopenta [b]indoles and pyrrolo[1,2-a]indoles.
- Source :
- SCIENCE CHINA Chemistry; 2021, Vol. 64 Issue 1, p34-40, 7p
- Publication Year :
- 2021
-
Abstract
- 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-π-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-π-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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 16747291
- Volume :
- 64
- Issue :
- 1
- Database :
- Complementary Index
- Journal :
- SCIENCE CHINA Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 148114475
- Full Text :
- https://doi.org/10.1007/s11426-020-9854-3