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Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis.
- Author(s): Ye, Chen-Xi
- Chen, Shuming
- Han, Feng
- Xie, Xiulan
- Ivlev, Sergei
- Houk, KN
- Meggers, Eric
- et al.
Published Web Location
https://doi.org/10.1002/anie.202004799Abstract
A transformation of fluxional into configurationally stable axially chiral N-arylpyrroles was achieved with a highly atroposelective electrophilic aromatic substitution catalyzed by a chiral-at-metal rhodium Lewis acid. Specifically, N-arylpyrroles were alkylated with N-acryloyl-1H-pyrazole electrophiles in up to 93 % yield and with up to >99.5 % ee, and follow-up conversions reveal the synthetic utility of this new method. DFT calculations elucidate the origins of the observed excellent atroposelectivity.
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