Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel–Crafts/Lactonization Reaction
Тип публикации: Journal Article
Дата публикации: 2015-09-24
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5
ISSN: 15237060, 15237052
PubMed ID:
26400069
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
A highly enantioselective and regioselective chiral Lewis acid catalyzed tandem Friedel-Crafts/lactonization reaction is reported, providing direct access to plenty of 3-hydroxy-3-trifluoromethyl benzofuran-2-ones in up to 94% yields with up to >99% ee. Mechanistic study reveals that the interactions between the phenolic hydroxyl group and trifluoropyruvate are the most likely contributing factor to the high enantio- and regioselectivity. Optically pure (-)-BHFF can be obtained in gram-scale with 0.05 mol % catalyst, demonstrating the potentially utility of this method in medicinal chemistry.
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ГОСТ
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Ren H. et al. Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel–Crafts/Lactonization Reaction // Organic Letters. 2015. Vol. 17. No. 19. pp. 4886-4889.
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Ren H., Wang P., Wang L., Tang Y. Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel–Crafts/Lactonization Reaction // Organic Letters. 2015. Vol. 17. No. 19. pp. 4886-4889.
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TY - JOUR
DO - 10.1021/acs.orglett.5b02440
UR - https://doi.org/10.1021/acs.orglett.5b02440
TI - Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel–Crafts/Lactonization Reaction
T2 - Organic Letters
AU - Ren, Hai
AU - Wang, Pan
AU - Wang, Lijia
AU - Tang, Yong
PY - 2015
DA - 2015/09/24
PB - American Chemical Society (ACS)
SP - 4886-4889
IS - 19
VL - 17
PMID - 26400069
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (до 50 авторов)
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@article{2015_Ren,
author = {Hai Ren and Pan Wang and Lijia Wang and Yong Tang},
title = {Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel–Crafts/Lactonization Reaction},
journal = {Organic Letters},
year = {2015},
volume = {17},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.orglett.5b02440},
number = {19},
pages = {4886--4889},
doi = {10.1021/acs.orglett.5b02440}
}
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MLA
Скопировать
Ren, Hai, et al. “Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel–Crafts/Lactonization Reaction.” Organic Letters, vol. 17, no. 19, Sep. 2015, pp. 4886-4889. https://doi.org/10.1021/acs.orglett.5b02440.