Alkylidene Meldrum's Acid as Acceptor‐Donor‐Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3‐b]pyrrolidine
Publication type: Journal Article
Publication date: 2023-09-26
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
Catalysis
Organic Chemistry
Abstract
A quinine‐derived thiourea‐catalyzed enantioselective double annulation strategy using alkylidene Meldrum′s acid as an acceptor‐donor‐acceptor with salicylaldehyde‐derived azomethine ylide is reported. The methodology is realized via a (3+2) cycloaddition/transesterification/decarboxylation sequence, giving chromeno[4,3‐b]pyrrolidines within 15–420 minutes at room temperature in 51–97% yields with 92–99% ee under 1–10 mol% catalyst loading. A plausible activation model is proposed for the excellent stereoinduction by H‐bond interaction between the catalyst and the Meldrum′s acid motif according to control experiments.
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Total citations:
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Citations from 2025:
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(33.33%)
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Liou Y. C. et al. Alkylidene Meldrum's Acid as Acceptor‐Donor‐Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3‐b]pyrrolidine // Advanced Synthesis and Catalysis. 2023. Vol. 365. No. 21. pp. 3603-3610.
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Liou Y. C., Chen Y. R., Hsu C., Huang X. R., Wang H., Lin W. Alkylidene Meldrum's Acid as Acceptor‐Donor‐Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3‐b]pyrrolidine // Advanced Synthesis and Catalysis. 2023. Vol. 365. No. 21. pp. 3603-3610.
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TY - JOUR
DO - 10.1002/adsc.202300609
UR - https://doi.org/10.1002/adsc.202300609
TI - Alkylidene Meldrum's Acid as Acceptor‐Donor‐Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3‐b]pyrrolidine
T2 - Advanced Synthesis and Catalysis
AU - Liou, Yan Cheng
AU - Chen, Yi Ru
AU - Hsu, Ching-Wen
AU - Huang, Xuan Rui
AU - Wang, Heng-Wei
AU - Lin, Wenwei
PY - 2023
DA - 2023/09/26
PB - Wiley
SP - 3603-3610
IS - 21
VL - 365
SN - 1615-4150
SN - 1615-4169
ER -
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@article{2023_Liou,
author = {Yan Cheng Liou and Yi Ru Chen and Ching-Wen Hsu and Xuan Rui Huang and Heng-Wei Wang and Wenwei Lin},
title = {Alkylidene Meldrum's Acid as Acceptor‐Donor‐Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3‐b]pyrrolidine},
journal = {Advanced Synthesis and Catalysis},
year = {2023},
volume = {365},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/adsc.202300609},
number = {21},
pages = {3603--3610},
doi = {10.1002/adsc.202300609}
}
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MLA
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Liou, Yan Cheng, et al. “Alkylidene Meldrum's Acid as Acceptor‐Donor‐Acceptor with Azomethine Ylide for Organocatalytic Asymmetric (3+2) Cycloaddition/Annulation: Synthesis of Chromeno[4,3‐b]pyrrolidine.” Advanced Synthesis and Catalysis, vol. 365, no. 21, Sep. 2023, pp. 3603-3610. https://doi.org/10.1002/adsc.202300609.