Diversity-Oriented Synthesis of Spirooxindoles via Asymmetric Organocatalytic Regiodivergent Cascade Reactions
2
Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266237, China
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Publication type: Journal Article
Publication date: 2024-12-06
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
39639609
Abstract
A regiodivergent strategy for the asymmetric diversity-oriented synthesis of spirooxindoles via organocatalytic cascade reactions is developed. Two regioselective pathways can be precisely controlled with different aminocatalysts in the reaction of 2-hydroxycinnamaldehydes and β,β-disubstituted 3-alkylidene oxindoles. The cascade vinylogous Michael/oxa-Michael/aldol reactions gave spiro-bridged oxindoles bearing two adjacent quaternary stereocenters, while the cascade oxa-Michael/Michael reactions gave spirooxindoles. Moreover, during the synthetic application studies, an acid-catalyzed rearrangement of spiro-bridged oxindoles was found to yield biologically important 3-alkylidene oxindoles.
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Ming Y. et al. Diversity-Oriented Synthesis of Spirooxindoles via Asymmetric Organocatalytic Regiodivergent Cascade Reactions // Organic Letters. 2024. Vol. 26. No. 50. pp. 10853-10858.
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Ming Y., LV X., Wang C., Liu Y. Diversity-Oriented Synthesis of Spirooxindoles via Asymmetric Organocatalytic Regiodivergent Cascade Reactions // Organic Letters. 2024. Vol. 26. No. 50. pp. 10853-10858.
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TY - JOUR
DO - 10.1021/acs.orglett.4c03993
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c03993
TI - Diversity-Oriented Synthesis of Spirooxindoles via Asymmetric Organocatalytic Regiodivergent Cascade Reactions
T2 - Organic Letters
AU - Ming, Yong-Chao
AU - LV, XUE-JIAO
AU - Wang, Chen
AU - Liu, Yankai
PY - 2024
DA - 2024/12/06
PB - American Chemical Society (ACS)
SP - 10853-10858
IS - 50
VL - 26
PMID - 39639609
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2024_Ming,
author = {Yong-Chao Ming and XUE-JIAO LV and Chen Wang and Yankai Liu},
title = {Diversity-Oriented Synthesis of Spirooxindoles via Asymmetric Organocatalytic Regiodivergent Cascade Reactions},
journal = {Organic Letters},
year = {2024},
volume = {26},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c03993},
number = {50},
pages = {10853--10858},
doi = {10.1021/acs.orglett.4c03993}
}
Cite this
MLA
Copy
Ming, Yong-Chao, et al. “Diversity-Oriented Synthesis of Spirooxindoles via Asymmetric Organocatalytic Regiodivergent Cascade Reactions.” Organic Letters, vol. 26, no. 50, Dec. 2024, pp. 10853-10858. https://pubs.acs.org/doi/10.1021/acs.orglett.4c03993.