Asymmetric Synthesis of Spiropyrazolones by Rhodium-Catalyzed C(sp2)-H Functionalization/Annulation Reactions.
Angew Chem Int Ed Engl. 2017 04 10; 56(16):4540-4544.AC

Abstract

Rhodium-catalyzed C(sp2)-H functionalization reactions of 4-aryl-5-pyrazolones followed by [3+2] annulation reactions with alkynes provide rapid access to highly enantioenriched five-membered-ring 4-spiro-5-pyrazolones. The use of a chiral SCpRh catalyst enabled the synthesis of a large range of spiropyrazolones with all-carbon quaternary stereogenic centers in up to 99 % yield and 98 % ee from readily available substrates.

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Authors+Show Affiliations

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300072, China.

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

28328101

Citation

Zheng, Jun, et al. "Asymmetric Synthesis of Spiropyrazolones By Rhodium-Catalyzed C(sp2)-H Functionalization/Annulation Reactions." Angewandte Chemie (International Ed. in English), vol. 56, no. 16, 2017, pp. 4540-4544.

Zheng J, Wang SB, Zheng C, et al. Asymmetric Synthesis of Spiropyrazolones by Rhodium-Catalyzed C(sp2)-H Functionalization/Annulation Reactions. Angew Chem Int Ed Engl. 2017;56(16):4540-4544.

Zheng, J., Wang, S. B., Zheng, C., & You, S. L. (2017). Asymmetric Synthesis of Spiropyrazolones by Rhodium-Catalyzed C(sp2)-H Functionalization/Annulation Reactions. Angewandte Chemie (International Ed. in English), 56(16), 4540-4544. https://doi.org/10.1002/anie.201700021

Zheng J, et al. Asymmetric Synthesis of Spiropyrazolones By Rhodium-Catalyzed C(sp2)-H Functionalization/Annulation Reactions. Angew Chem Int Ed Engl. 2017 04 10;56(16):4540-4544. PubMed PMID: 28328101.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Asymmetric Synthesis of Spiropyrazolones by Rhodium-Catalyzed C(sp2)-H Functionalization/Annulation Reactions. AU - Zheng,Jun, AU - Wang,Shao-Bo, AU - Zheng,Chao, AU - You,Shu-Li, Y1 - 2017/03/22/ PY - 2017/01/02/received PY - 2017/02/27/revised PY - 2017/3/23/pubmed PY - 2017/3/23/medline PY - 2017/3/23/entrez KW - C-H functionalization KW - alkynes KW - asymmetric catalysis KW - pyrazolones KW - rhodium SP - 4540 EP - 4544 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 56 IS - 16 N2 - Rhodium-catalyzed C(sp2)-H functionalization reactions of 4-aryl-5-pyrazolones followed by [3+2] annulation reactions with alkynes provide rapid access to highly enantioenriched five-membered-ring 4-spiro-5-pyrazolones. The use of a chiral SCpRh catalyst enabled the synthesis of a large range of spiropyrazolones with all-carbon quaternary stereogenic centers in up to 99 % yield and 98 % ee from readily available substrates. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/28328101/Asymmetric_Synthesis_of_Spiropyrazolones_by_Rhodium_Catalyzed_C_sp2__H_Functionalization/Annulation_Reactions_ L2 - https://doi.org/10.1002/anie.201700021 DB - PRIME DP - Unbound Medicine ER -

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Asymmetric Synthesis of Spiropyrazolones by Rhodium-Catalyzed C(sp2)-H Functionalization/Annulation Reactions.Angew Chem Int Ed Engl. 2017 04 10; 56(16):4540-4544.AC