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Issue 44, 2021
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Enantioselective synthesis of polycyclic pyrrole derivatives by iridium-catalyzed asymmetric allylic dearomatization and ring-expansive migration reactions

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Abstract

Herein, we report an N-alkylation of pyrroles triggered by an unprecedented selective ring-expansive migration of the spiro-2H-pyrrole intermediates obtained via Ir-catalyzed asymmetric allylic dearomatization. The reaction affords a series of tetrahydropyrrolo[1,2-c]pyrimidine derivatives in good yields (up to 88%) with excellent enantioselectivity (up to >99% ee). The proposed reaction mechanism is supported by DFT calculations and the characterization of the key intermediate.

Graphical abstract: Enantioselective synthesis of polycyclic pyrrole derivatives by iridium-catalyzed asymmetric allylic dearomatization and ring-expansive migration reactions

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Article information


Submitted
12 Apr 2021
Accepted
27 Apr 2021
First published
28 Apr 2021

Chem. Commun., 2021,57, 5390-5393
Article type
Communication

Enantioselective synthesis of polycyclic pyrrole derivatives by iridium-catalyzed asymmetric allylic dearomatization and ring-expansive migration reactions

L. Huang, J. Xie, Y. Cai, C. Zheng, X. Hou, L. Dai and S. You, Chem. Commun., 2021, 57, 5390
DOI: 10.1039/D1CC01929E

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