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N-Heterocyclic carbene-catalyzed enantioselective hetero-[10 + 2] annulation.
- Source :
- Communications Chemistry; 11/27/2020, Vol. 3 Issue 1, pN.PAG-N.PAG, 1p
- Publication Year :
- 2020
-
Abstract
- Higher-order cycloadditions are a powerful strategy for the construction of polycycles in one step. However, an efficient and concise version for the induction of asymmetry is lacking. N-heterocyclic carbenes are widely used organocatalysts for asymmetric synthesis and could be an ideal choice for enantioselective higher-order cycloadditions. Here, we report an enantioselective [10 + 2] annulation between catalytically formed aza-benzofulvene intermediates and trifluoromethyl ketone derivatives. This protocol exhibits a wide scope, high yields, and good ee values, reflecting a robust and efficient higher-order cycloaddition. Density functional theory calculations provide an accurate prediction of the reaction enantioselectivity, and in-depth insight to the origins of stereocontrol. High-order cycloaddition reactions are useful for the construction of polycycles in a single step, but versions that induce asymmetry are limited. Here the authors report the construction of asymmetric polycycles via N-heterocyclic carbene-catalyzed hetero-[10 + 2] cycloaddition of indole-2-carbaldehydes with trifluoromethyl ketone derivatives. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 23993669
- Volume :
- 3
- Issue :
- 1
- Database :
- Complementary Index
- Journal :
- Communications Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 147251303
- Full Text :
- https://doi.org/10.1038/s42004-020-00425-7