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Rhodium-Catalyzed [4 + 1] Cyclization via C-H Activation for the Synthesis of Divergent Heterocycles Bearing a Quaternary Carbon.
J Org Chem. 2018 04 20; 83(8):4650-4656.JO

Abstract

The development of an efficient approach to construct fused polycyclic systems bearing a quaternary carbon center represents a great challenge to synthetic chemistry. Herein, we report a Rh(III)-catalyzed [4 + 1] annulation of propargyl alcohols with various heterocyclic scaffolds under an air atmosphere. Diverse fused heterocycles containing a quaternary carbon center were obtained in moderate to good yields. Additionally, this method features a high atom-economy, metal oxidant free, simple operation, and compatibility with various functional groups.

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Authors+Show Affiliations

Wu X
Drug Discovery Department , H. Lee Moffitt Cancer Center and Research Institute , 12902 Magnolia Drive , Tampa , Florida 33612-9416 , United States.
Ji H
Drug Discovery Department , H. Lee Moffitt Cancer Center and Research Institute , 12902 Magnolia Drive , Tampa , Florida 33612-9416 , United States. Departments of Oncologic Sciences and Chemistry , University of South Florida , Tampa , Florida 33612 , United States.

MeSH

AlkynesCarbonCatalysisChemistry Techniques, SyntheticCyclizationHeterocyclic CompoundsPropanolsRhodium

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

29608841

Citation

Wu, Xiaowei, and Haitao Ji. "Rhodium-Catalyzed [4 + 1] Cyclization Via C-H Activation for the Synthesis of Divergent Heterocycles Bearing a Quaternary Carbon." The Journal of Organic Chemistry, vol. 83, no. 8, 2018, pp. 4650-4656.
Wu X, Ji H. Rhodium-Catalyzed [4 + 1] Cyclization via C-H Activation for the Synthesis of Divergent Heterocycles Bearing a Quaternary Carbon. J Org Chem. 2018;83(8):4650-4656.
Wu, X., & Ji, H. (2018). Rhodium-Catalyzed [4 + 1] Cyclization via C-H Activation for the Synthesis of Divergent Heterocycles Bearing a Quaternary Carbon. The Journal of Organic Chemistry, 83(8), 4650-4656. https://doi.org/10.1021/acs.joc.8b00397
Wu X, Ji H. Rhodium-Catalyzed [4 + 1] Cyclization Via C-H Activation for the Synthesis of Divergent Heterocycles Bearing a Quaternary Carbon. J Org Chem. 2018 04 20;83(8):4650-4656. PubMed PMID: 29608841.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-Catalyzed [4 + 1] Cyclization via C-H Activation for the Synthesis of Divergent Heterocycles Bearing a Quaternary Carbon. AU - Wu,Xiaowei, AU - Ji,Haitao, Y1 - 2018/04/09/ PY - 2018/4/3/pubmed PY - 2018/7/3/medline PY - 2018/4/3/entrez SP - 4650 EP - 4656 JF - The Journal of organic chemistry JO - J Org Chem VL - 83 IS - 8 N2 - The development of an efficient approach to construct fused polycyclic systems bearing a quaternary carbon center represents a great challenge to synthetic chemistry. Herein, we report a Rh(III)-catalyzed [4 + 1] annulation of propargyl alcohols with various heterocyclic scaffolds under an air atmosphere. Diverse fused heterocycles containing a quaternary carbon center were obtained in moderate to good yields. Additionally, this method features a high atom-economy, metal oxidant free, simple operation, and compatibility with various functional groups. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/29608841/Rhodium_Catalyzed_[4_+_1]_Cyclization_via_C_H_Activation_for_the_Synthesis_of_Divergent_Heterocycles_Bearing_a_Quaternary_Carbon_ DB - PRIME DP - Unbound Medicine ER -