Asymmetric Intramolecular Dearomatization of Nonactivated Arenes with Ynamides for Rapid Assembly of Fused Ring System under Silver Catalysis
Tsubasa Ito
1
,
Shingo Harada
1
,
Haruka Homma
1
,
Hiroki Takenaka
1
,
Shumpei Hirose
1
,
Tetsuhiro Nemoto
1, 2
Publication type: Journal Article
Publication date: 2020-12-31
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
33382259
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Arene dearomatization is a straightforward method for converting an aromatic feedstock into functionalized carbocycles. Enantioselective dearomatizations of chemically inert arenes, however, are quite limited and underexplored relative to those of phenols and indoles. We developed a method for diazo-free generation of silver-carbene species from an ynamide and applied it to the dearomatization of nonactivated arenes. Transiently generated norcaradiene could be trapped by intermolecular [4 + 2] cycloaddition, synthesizing polycycles with five consecutive stereogenic centers. This protocol constitutes the first highly enantioselective reaction based on the diazo-free generation of silver-carbene species. Mechanistic investigations revealed a dearomatization followed by two different classes of pericyclic reactions, as well as the origin of the chemo- and enantioselectivity.
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GOST
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Ito T. et al. Asymmetric Intramolecular Dearomatization of Nonactivated Arenes with Ynamides for Rapid Assembly of Fused Ring System under Silver Catalysis // Journal of the American Chemical Society. 2020. Vol. 143. No. 2. pp. 604-611.
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Ito T., Harada S., Homma H., Takenaka H., Hirose S., Nemoto T. Asymmetric Intramolecular Dearomatization of Nonactivated Arenes with Ynamides for Rapid Assembly of Fused Ring System under Silver Catalysis // Journal of the American Chemical Society. 2020. Vol. 143. No. 2. pp. 604-611.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jacs.0c10682
UR - https://doi.org/10.1021/jacs.0c10682
TI - Asymmetric Intramolecular Dearomatization of Nonactivated Arenes with Ynamides for Rapid Assembly of Fused Ring System under Silver Catalysis
T2 - Journal of the American Chemical Society
AU - Ito, Tsubasa
AU - Harada, Shingo
AU - Homma, Haruka
AU - Takenaka, Hiroki
AU - Hirose, Shumpei
AU - Nemoto, Tetsuhiro
PY - 2020
DA - 2020/12/31
PB - American Chemical Society (ACS)
SP - 604-611
IS - 2
VL - 143
PMID - 33382259
SN - 0002-7863
SN - 1520-5126
ER -
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BibTex (up to 50 authors)
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@article{2020_Ito,
author = {Tsubasa Ito and Shingo Harada and Haruka Homma and Hiroki Takenaka and Shumpei Hirose and Tetsuhiro Nemoto},
title = {Asymmetric Intramolecular Dearomatization of Nonactivated Arenes with Ynamides for Rapid Assembly of Fused Ring System under Silver Catalysis},
journal = {Journal of the American Chemical Society},
year = {2020},
volume = {143},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/jacs.0c10682},
number = {2},
pages = {604--611},
doi = {10.1021/jacs.0c10682}
}
Cite this
MLA
Copy
Ito, Tsubasa, et al. “Asymmetric Intramolecular Dearomatization of Nonactivated Arenes with Ynamides for Rapid Assembly of Fused Ring System under Silver Catalysis.” Journal of the American Chemical Society, vol. 143, no. 2, Dec. 2020, pp. 604-611. https://doi.org/10.1021/jacs.0c10682.