Journal of Organic Chemistry, volume 85, issue 2, pages 430-440

Sc(OTf)3-Catalyzed Chemodivergent Annulations of γ-Butyrolactone-Fused Cyclopropanes with Anthranils

Publication typeJournal Article
Publication date2019-12-05
Q2
Q1
SJR0.724
CiteScore6.2
Impact factor3.3
ISSN00223263, 15206904
Organic Chemistry
Abstract
The Lewis acid-catalyzed annulations between anthranils and γ-butyrolactone-fused donor-acceptor cyclopropanes have been developed. Depending on the anthranils used, such annulations proceeded in a chemodivergent way to produce either bridged cyclic products via [4 + 3] annulation or γ-butyrolactone-fused tetrahydroquinoline products via a cascade process in moderate to high yields. A probable mechanism for the two reaction pathways has been proposed. The reaction could be performed on a gram-scale, and the products could be elaborated to other useful cyclic structures bearing multiple contiguous stereogenic centers.
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GOST |
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GOST Copy
Zhang X. et al. Sc(OTf)3-Catalyzed Chemodivergent Annulations of γ-Butyrolactone-Fused Cyclopropanes with Anthranils // Journal of Organic Chemistry. 2019. Vol. 85. No. 2. pp. 430-440.
GOST all authors (up to 50) Copy
Zhang X., Feng M., Yang G., Chai Z. Sc(OTf)3-Catalyzed Chemodivergent Annulations of γ-Butyrolactone-Fused Cyclopropanes with Anthranils // Journal of Organic Chemistry. 2019. Vol. 85. No. 2. pp. 430-440.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.joc.9b02444
UR - https://doi.org/10.1021/acs.joc.9b02444
TI - Sc(OTf)3-Catalyzed Chemodivergent Annulations of γ-Butyrolactone-Fused Cyclopropanes with Anthranils
T2 - Journal of Organic Chemistry
AU - Zhang, Xingyu
AU - Feng, Manli
AU - Yang, Gaosheng
AU - Chai, Zhuo
PY - 2019
DA - 2019/12/05
PB - American Chemical Society (ACS)
SP - 430-440
IS - 2
VL - 85
SN - 0022-3263
SN - 1520-6904
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Zhang,
author = {Xingyu Zhang and Manli Feng and Gaosheng Yang and Zhuo Chai},
title = {Sc(OTf)3-Catalyzed Chemodivergent Annulations of γ-Butyrolactone-Fused Cyclopropanes with Anthranils},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.joc.9b02444},
number = {2},
pages = {430--440},
doi = {10.1021/acs.joc.9b02444}
}
MLA
Cite this
MLA Copy
Zhang, Xingyu, et al. “Sc(OTf)3-Catalyzed Chemodivergent Annulations of γ-Butyrolactone-Fused Cyclopropanes with Anthranils.” Journal of Organic Chemistry, vol. 85, no. 2, Dec. 2019, pp. 430-440. https://doi.org/10.1021/acs.joc.9b02444.
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