Asymmetric (3 + 3) and (4 + 2) Annulation Reactions of 2,3-Dioxopyrrolidines with 3-Alkylidene Oxindoles to Construct Diverse Chiral Heterocyclic Frameworks
Publication type: Journal Article
Publication date: 2024-06-08
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
38850251
Abstract
Two substrate-controlled regiodivergent annulation protocols for 2,3-dioxopyrrolidines with 3-alkylidene oxindoles have been developed, which furnished a series of fused dihydropyrrolidone derivatives in high yields with excellent stereoselectivities. Plausible mechanistic pathways for both annulation reactions are proposed that [3 + 3] annulation reaction involves vinylogous Michael addition followed by intramolecular aldol cyclization, while [4 + 2] annulation reaction occurs through a vinylogous Michael addition and a subsequent intramolecular oxa-Michael cyclization.
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7
Total citations:
7
Citations from 2024:
7
(100%)
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Huang S. et al. Asymmetric (3 + 3) and (4 + 2) Annulation Reactions of 2,3-Dioxopyrrolidines with 3-Alkylidene Oxindoles to Construct Diverse Chiral Heterocyclic Frameworks // Journal of Organic Chemistry. 2024. Vol. 89. No. 12. pp. 8970-8984.
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Huang S., Chen I., Chen I. T., Han J. L. Asymmetric (3 + 3) and (4 + 2) Annulation Reactions of 2,3-Dioxopyrrolidines with 3-Alkylidene Oxindoles to Construct Diverse Chiral Heterocyclic Frameworks // Journal of Organic Chemistry. 2024. Vol. 89. No. 12. pp. 8970-8984.
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TY - JOUR
DO - 10.1021/acs.joc.4c00933
UR - https://pubs.acs.org/doi/10.1021/acs.joc.4c00933
TI - Asymmetric (3 + 3) and (4 + 2) Annulation Reactions of 2,3-Dioxopyrrolidines with 3-Alkylidene Oxindoles to Construct Diverse Chiral Heterocyclic Frameworks
T2 - Journal of Organic Chemistry
AU - Huang, Shi-Hang
AU - Chen, I-Ting
AU - Chen, I Ting
AU - Han, Jeng Liang
PY - 2024
DA - 2024/06/08
PB - American Chemical Society (ACS)
SP - 8970-8984
IS - 12
VL - 89
PMID - 38850251
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2024_Huang,
author = {Shi-Hang Huang and I-Ting Chen and I Ting Chen and Jeng Liang Han},
title = {Asymmetric (3 + 3) and (4 + 2) Annulation Reactions of 2,3-Dioxopyrrolidines with 3-Alkylidene Oxindoles to Construct Diverse Chiral Heterocyclic Frameworks},
journal = {Journal of Organic Chemistry},
year = {2024},
volume = {89},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.4c00933},
number = {12},
pages = {8970--8984},
doi = {10.1021/acs.joc.4c00933}
}
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Huang, Shi-Hang, et al. “Asymmetric (3 + 3) and (4 + 2) Annulation Reactions of 2,3-Dioxopyrrolidines with 3-Alkylidene Oxindoles to Construct Diverse Chiral Heterocyclic Frameworks.” Journal of Organic Chemistry, vol. 89, no. 12, Jun. 2024, pp. 8970-8984. https://pubs.acs.org/doi/10.1021/acs.joc.4c00933.