Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols
XUE-SONG LI
1
,
Xiangtao Kong
2
,
Cui Tian Wang
1
,
Zhi Jie Niu
1
,
Wan Xu Wei
1
,
Hong Chao Liu
1
,
Zhe Zhang
1
,
Yuke Li
3
,
Yong-Min Liang
1
Publication type: Journal Article
Publication date: 2021-12-03
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
34859669
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A new method for the efficient synthesis of hexahydro-1H-fluorene and octahydrobenzo[a]azulene derivatives through a ring-expansion strategy is reported. With an appropriate combination of thulium(III) trifluoromethanesulfonate and 13X molecular sieves, a range of unsaturated polycyclic compounds were obtained in good yields. Mechanism studies reveal that the reaction is more likely to undergo Meyer-Schuster rearrangement, ring expansion, and Friedel-Crafts-type pathways, which provide a conceptually different strategy for the ring opening of tertiary cycloalkanols.
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13
Total citations:
13
Citations from 2024:
7
(53%)
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GOST
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LI X. et al. Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols // Organic Letters. 2021. Vol. 23. No. 24. pp. 9457-9462.
GOST all authors (up to 50)
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LI X., Kong X., Wang C. T., Niu Z. J., Wei W. X., Liu H. C., Zhang Z., Li Y., Liang Y. Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols // Organic Letters. 2021. Vol. 23. No. 24. pp. 9457-9462.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.1c03621
UR - https://doi.org/10.1021/acs.orglett.1c03621
TI - Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols
T2 - Organic Letters
AU - LI, XUE-SONG
AU - Kong, Xiangtao
AU - Wang, Cui Tian
AU - Niu, Zhi Jie
AU - Wei, Wan Xu
AU - Liu, Hong Chao
AU - Zhang, Zhe
AU - Li, Yuke
AU - Liang, Yong-Min
PY - 2021
DA - 2021/12/03
PB - American Chemical Society (ACS)
SP - 9457-9462
IS - 24
VL - 23
PMID - 34859669
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2021_LI,
author = {XUE-SONG LI and Xiangtao Kong and Cui Tian Wang and Zhi Jie Niu and Wan Xu Wei and Hong Chao Liu and Zhe Zhang and Yuke Li and Yong-Min Liang},
title = {Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols},
journal = {Organic Letters},
year = {2021},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.orglett.1c03621},
number = {24},
pages = {9457--9462},
doi = {10.1021/acs.orglett.1c03621}
}
Cite this
MLA
Copy
LI, XUE-SONG, et al. “Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols.” Organic Letters, vol. 23, no. 24, Dec. 2021, pp. 9457-9462. https://doi.org/10.1021/acs.orglett.1c03621.