Journal
CHEMICAL COMMUNICATIONS
Volume 57, Issue 44, Pages 5390-5393Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc01929e
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Funding
- NSFC [21772219, 21821002, 22031012, 91856201]
- Science and Technology Commission of Shanghai Municipality [18QA1404900, 19590750400]
- Youth Innovation Promotion Association of CAS [2017302]
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This study presents a novel N-alkylation of pyrroles through an Ir-catalyzed asymmetric allylic dearomatization-induced selective ring-expansive migration, providing a series of tetrahydropyrrolo[1,2-c]pyrimidine derivatives with good yields and excellent enantioselectivity. The proposed reaction mechanism is supported by DFT calculations and the characterization of the key intermediate.
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.
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