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Gold-Catalyzed Intramolecular Dearomatization Reactions of Indoles for the Synthesis of Spiroindolenines and Spiroindolines.
Org Lett. 2020 02 21; 22(4):1233-1238.OL

Abstract

A gold-catalyzed dearomatization reaction of indole derivatives was realized in the presence of JohnPhosAuCl/AgOMs to afford a series of spiroindolenines in excellent yields (≤99%). In addition, when the Hantzsch ester was used as the hydrogen transfer reagent, various spiroindolines were obtained in a cascade fashion starting from readily available indole derivatives in modest to good yields (≤79%). Both reactions feature readily available substrates, mild conditions, and good functional group tolerance.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wu WT
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 LinglingLu , Shanghai 200032 , China.
Ding L
School of Physical Science and Technology , ShanghaiTech University , 100 Haike Road , Shanghai 201210 , China.
Zhang L
Department of Chemistry & Biochemistry , University of California, Santa Barbara , Santa Barbara , California 93106 , United States.
You SL
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 LinglingLu , Shanghai 200032 , China. School of Physical Science and Technology , ShanghaiTech University , 100 Haike Road , Shanghai 201210 , China.

MeSH

CatalysisGoldIndolesMolecular StructureSpiro CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

31789039

Citation

Wu, Wen-Ting, et al. "Gold-Catalyzed Intramolecular Dearomatization Reactions of Indoles for the Synthesis of Spiroindolenines and Spiroindolines." Organic Letters, vol. 22, no. 4, 2020, pp. 1233-1238.
Wu WT, Ding L, Zhang L, et al. Gold-Catalyzed Intramolecular Dearomatization Reactions of Indoles for the Synthesis of Spiroindolenines and Spiroindolines. Org Lett. 2020;22(4):1233-1238.
Wu, W. T., Ding, L., Zhang, L., & You, S. L. (2020). Gold-Catalyzed Intramolecular Dearomatization Reactions of Indoles for the Synthesis of Spiroindolenines and Spiroindolines. Organic Letters, 22(4), 1233-1238. https://doi.org/10.1021/acs.orglett.9b03988
Wu WT, et al. Gold-Catalyzed Intramolecular Dearomatization Reactions of Indoles for the Synthesis of Spiroindolenines and Spiroindolines. Org Lett. 2020 02 21;22(4):1233-1238. PubMed PMID: 31789039.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Gold-Catalyzed Intramolecular Dearomatization Reactions of Indoles for the Synthesis of Spiroindolenines and Spiroindolines. AU - Wu,Wen-Ting, AU - Ding,Lu, AU - Zhang,Liming, AU - You,Shu-Li, Y1 - 2019/12/02/ PY - 2019/12/4/pubmed PY - 2020/11/18/medline PY - 2019/12/3/entrez SP - 1233 EP - 1238 JF - Organic letters JO - Org Lett VL - 22 IS - 4 N2 - A gold-catalyzed dearomatization reaction of indole derivatives was realized in the presence of JohnPhosAuCl/AgOMs to afford a series of spiroindolenines in excellent yields (≤99%). In addition, when the Hantzsch ester was used as the hydrogen transfer reagent, various spiroindolines were obtained in a cascade fashion starting from readily available indole derivatives in modest to good yields (≤79%). Both reactions feature readily available substrates, mild conditions, and good functional group tolerance. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/31789039/Gold_Catalyzed_Intramolecular_Dearomatization_Reactions_of_Indoles_for_the_Synthesis_of_Spiroindolenines_and_Spiroindolines_ DB - PRIME DP - Unbound Medicine ER -