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Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis.

ABSTRACT: 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.

SUBMITTER: Ye CX 

PROVIDER: S-EPMC7496906 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis.

Ye Chen-Xi CX   Chen Shuming S   Han Feng F   Xie Xiulan X   Ivlev Sergei S   Houk K N KN   Meggers Eric E  

Angewandte Chemie (International ed. in English) 20200603 32

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 atropos  ...[more]

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