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Enantioselective synthesis of polycyclic pyrrole derivatives by iridium-catalyzed asymmetric allylic dearomatization and ring-expansive migration reactions.
Chem Commun (Camb). 2021 Jun 01; 57(44):5390-5393.CC

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.

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Authors+Show Affiliations

Huang L
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China. zhengchao@sioc.ac.cn slyou@sioc.ac.cn.
Xie JH
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China. zhengchao@sioc.ac.cn slyou@sioc.ac.cn.
Cai Y
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China. zhengchao@sioc.ac.cn slyou@sioc.ac.cn.
Zheng C
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China. zhengchao@sioc.ac.cn slyou@sioc.ac.cn.
Hou XL
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China. zhengchao@sioc.ac.cn slyou@sioc.ac.cn.
Dai LX
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China. zhengchao@sioc.ac.cn slyou@sioc.ac.cn.
You SL
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China. zhengchao@sioc.ac.cn slyou@sioc.ac.cn.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

33949525

Citation

Huang, Lin, et al. "Enantioselective Synthesis of Polycyclic Pyrrole Derivatives By Iridium-catalyzed Asymmetric Allylic Dearomatization and Ring-expansive Migration Reactions." Chemical Communications (Cambridge, England), vol. 57, no. 44, 2021, pp. 5390-5393.
Huang L, Xie JH, Cai Y, et al. Enantioselective synthesis of polycyclic pyrrole derivatives by iridium-catalyzed asymmetric allylic dearomatization and ring-expansive migration reactions. Chem Commun (Camb). 2021;57(44):5390-5393.
Huang, L., Xie, J. H., Cai, Y., Zheng, C., Hou, X. L., Dai, L. X., & You, S. L. (2021). Enantioselective synthesis of polycyclic pyrrole derivatives by iridium-catalyzed asymmetric allylic dearomatization and ring-expansive migration reactions. Chemical Communications (Cambridge, England), 57(44), 5390-5393. https://doi.org/10.1039/d1cc01929e
Huang L, et al. Enantioselective Synthesis of Polycyclic Pyrrole Derivatives By Iridium-catalyzed Asymmetric Allylic Dearomatization and Ring-expansive Migration Reactions. Chem Commun (Camb). 2021 Jun 1;57(44):5390-5393. PubMed PMID: 33949525.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective synthesis of polycyclic pyrrole derivatives by iridium-catalyzed asymmetric allylic dearomatization and ring-expansive migration reactions. AU - Huang,Lin, AU - Xie,Jia-Hao, AU - Cai,Yue, AU - Zheng,Chao, AU - Hou,Xue-Long, AU - Dai,Li-Xin, AU - You,Shu-Li, PY - 2021/5/6/pubmed PY - 2021/5/6/medline PY - 2021/5/5/entrez SP - 5390 EP - 5393 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 57 IS - 44 N2 - 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. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/33949525/Enantioselective_synthesis_of_polycyclic_pyrrole_derivatives_by_iridium_catalyzed_asymmetric_allylic_dearomatization_and_ring_expansive_migration_reactions_ DB - PRIME DP - Unbound Medicine ER -
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