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Asymmetric Domino Heck/Dearomatization Reaction of β-Naphthols to Construct Indole-Terpenoid Frameworks.
Org Lett. 2021 Oct 15; 23(20):7865-7872.OL

Abstract

A palladium-catalyzed enantioselective Heck cyclization/dearomatization cascade via capturing the cyclized Heck π-allylpalladium intermediate by β-naphthols is reported, which provides a new strategy for the construction of chiral indole-terpenoid frameworks. This method affords indole-functionalized β-naphthalenone compounds bearing an all-carbon-substituted quaternary chiral center in excellent yields (up to 92%) and enantioselectivities (up to 94% ee). In addition, the utility of this method is showcased by the gram-scale syntheses and diverse transformations of the dearomatized products.

Authors+Show Affiliations

NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

34582193

Citation

Wang, Dong-Chao, et al. "Asymmetric Domino Heck/Dearomatization Reaction of β-Naphthols to Construct Indole-Terpenoid Frameworks." Organic Letters, vol. 23, no. 20, 2021, pp. 7865-7872.
Wang DC, Cheng PP, Yang TT, et al. Asymmetric Domino Heck/Dearomatization Reaction of β-Naphthols to Construct Indole-Terpenoid Frameworks. Org Lett. 2021;23(20):7865-7872.
Wang, D. C., Cheng, P. P., Yang, T. T., Wu, P. P., Qu, G. R., & Guo, H. M. (2021). Asymmetric Domino Heck/Dearomatization Reaction of β-Naphthols to Construct Indole-Terpenoid Frameworks. Organic Letters, 23(20), 7865-7872. https://doi.org/10.1021/acs.orglett.1c02881
Wang DC, et al. Asymmetric Domino Heck/Dearomatization Reaction of β-Naphthols to Construct Indole-Terpenoid Frameworks. Org Lett. 2021 Oct 15;23(20):7865-7872. PubMed PMID: 34582193.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric Domino Heck/Dearomatization Reaction of β-Naphthols to Construct Indole-Terpenoid Frameworks. AU - Wang,Dong-Chao, AU - Cheng,Peng-Peng, AU - Yang,Ting-Ting, AU - Wu,Pan-Pan, AU - Qu,Gui-Rong, AU - Guo,Hai-Ming, Y1 - 2021/09/28/ PY - 2021/9/29/pubmed PY - 2021/9/29/medline PY - 2021/9/28/entrez SP - 7865 EP - 7872 JF - Organic letters JO - Org Lett VL - 23 IS - 20 N2 - A palladium-catalyzed enantioselective Heck cyclization/dearomatization cascade via capturing the cyclized Heck π-allylpalladium intermediate by β-naphthols is reported, which provides a new strategy for the construction of chiral indole-terpenoid frameworks. This method affords indole-functionalized β-naphthalenone compounds bearing an all-carbon-substituted quaternary chiral center in excellent yields (up to 92%) and enantioselectivities (up to 94% ee). In addition, the utility of this method is showcased by the gram-scale syntheses and diverse transformations of the dearomatized products. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/34582193/Asymmetric_Domino_Heck/Dearomatization_Reaction_of_β_Naphthols_to_Construct_Indole_Terpenoid_Frameworks_ DB - PRIME DP - Unbound Medicine ER -
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