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.
Links
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 -