Lewis-Acid-Catalyzed Dearomative [4π + 2σ] Cycloaddition of Bicyclobutanes with Isoquinolinium Methylides for the Synthesis of Ring-Fused Azabicyclo[3.1.1]heptanes
Qin Jiang
1, 2
,
Jianyang Dong
1, 2, 3
,
Xuechen Zhou
1, 2, 4
,
HUIJUAN LIAO
1, 2, 4
,
Juan Zhou
1, 2
,
Dong Xue
1, 2, 3, 4, 5
1
School of Chemistry and Chemical Engineering, Xi’an, People’s Republic of China
|
3
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Xi’an, People’s Republic of China
|
Publication type: Journal Article
Publication date: 2024-10-17
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
39419592
Abstract
Dearomative cycloadditions are valuable for efficiently generating three-dimensional molecular complexity. However, despite recent reports of cycloadditions of bicyclobutanes (BCBs) for the synthesis of aza-bicyclo[3.1.1]heptanes (aza-BCHeps), which are bioisosteres of meta-substituted aza-arenes, dearomative cycloaddition of BCBs with N-heteroarenes for the synthesis of ring-fused aza-BCHeps has yet to be achieved. Herein, we disclose a method for Lewis acid–catalyzed [4π + 2σ] cycloaddition of isoquinolinium methylides with BCBs, which furnished a diverse array of previously inaccessible ring-fused 3-aza-BCHeps. We demonstrated the synthetic utility of the method by carrying out scaled-up reactions and transforming the products.
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15
Total citations:
15
Citations from 2025:
13
(86.67%)
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Jiang Q. et al. Lewis-Acid-Catalyzed Dearomative [4π + 2σ] Cycloaddition of Bicyclobutanes with Isoquinolinium Methylides for the Synthesis of Ring-Fused Azabicyclo[3.1.1]heptanes // Organic Letters. 2024. Vol. 26. No. 43. pp. 9311-9315.
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Jiang Q., Dong J., Zhou X., LIAO H., Zhou J., Xue D. Lewis-Acid-Catalyzed Dearomative [4π + 2σ] Cycloaddition of Bicyclobutanes with Isoquinolinium Methylides for the Synthesis of Ring-Fused Azabicyclo[3.1.1]heptanes // Organic Letters. 2024. Vol. 26. No. 43. pp. 9311-9315.
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TY - JOUR
DO - 10.1021/acs.orglett.4c03489
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c03489
TI - Lewis-Acid-Catalyzed Dearomative [4π + 2σ] Cycloaddition of Bicyclobutanes with Isoquinolinium Methylides for the Synthesis of Ring-Fused Azabicyclo[3.1.1]heptanes
T2 - Organic Letters
AU - Jiang, Qin
AU - Dong, Jianyang
AU - Zhou, Xuechen
AU - LIAO, HUIJUAN
AU - Zhou, Juan
AU - Xue, Dong
PY - 2024
DA - 2024/10/17
PB - American Chemical Society (ACS)
SP - 9311-9315
IS - 43
VL - 26
PMID - 39419592
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2024_Jiang,
author = {Qin Jiang and Jianyang Dong and Xuechen Zhou and HUIJUAN LIAO and Juan Zhou and Dong Xue},
title = {Lewis-Acid-Catalyzed Dearomative [4π + 2σ] Cycloaddition of Bicyclobutanes with Isoquinolinium Methylides for the Synthesis of Ring-Fused Azabicyclo[3.1.1]heptanes},
journal = {Organic Letters},
year = {2024},
volume = {26},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c03489},
number = {43},
pages = {9311--9315},
doi = {10.1021/acs.orglett.4c03489}
}
Cite this
MLA
Copy
Jiang, Qin, et al. “Lewis-Acid-Catalyzed Dearomative [4π + 2σ] Cycloaddition of Bicyclobutanes with Isoquinolinium Methylides for the Synthesis of Ring-Fused Azabicyclo[3.1.1]heptanes.” Organic Letters, vol. 26, no. 43, Oct. 2024, pp. 9311-9315. https://pubs.acs.org/doi/10.1021/acs.orglett.4c03489.