Diastereo- and Enantioselective Construction of 3,3′-Pyrrolidinyldispirooxindole Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions
Publication type: Journal Article
Publication date: 2015-05-14
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
25939045
Organic Chemistry
Abstract
The first catalytic enantioselective construction of a 3,3'-pyrrolidinyldispirooxindole scaffold has been established via organocatalytic asymmetric 1,3-dipolar cycloadditions of isatin-derived azomethine ylides with methyleneindolinones, which afforded structurally complex bis-spirooxindoles containing three contiguous and two quaternary stereogenic centers in generally high yields (up to 99%) and excellent diastereo- and enantioselectivities (up to >95:5 dr, 98% ee). This reaction also provides a good example for the application of catalytic asymmetric 1,3-dipolar cycloadditions in constructing enantioenriched bis-spirooxindole frameworks with structural complexity and rigidity.
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178
Total citations:
178
Citations from 2025:
7
(3.93%)
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GOST
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Dai W. et al. Diastereo- and Enantioselective Construction of 3,3′-Pyrrolidinyldispirooxindole Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions // Journal of Organic Chemistry. 2015. Vol. 80. No. 11. pp. 5737-5744.
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Dai W., Jiang X. L., Wu Q., Shi F., Jiang B. Diastereo- and Enantioselective Construction of 3,3′-Pyrrolidinyldispirooxindole Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions // Journal of Organic Chemistry. 2015. Vol. 80. No. 11. pp. 5737-5744.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.5b00708
UR - https://doi.org/10.1021/acs.joc.5b00708
TI - Diastereo- and Enantioselective Construction of 3,3′-Pyrrolidinyldispirooxindole Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions
T2 - Journal of Organic Chemistry
AU - Dai, Wei
AU - Jiang, Xiao Li
AU - Wu, Qiong
AU - Shi, Feng
AU - Jiang, Bo
PY - 2015
DA - 2015/05/14
PB - American Chemical Society (ACS)
SP - 5737-5744
IS - 11
VL - 80
PMID - 25939045
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2015_Dai,
author = {Wei Dai and Xiao Li Jiang and Qiong Wu and Feng Shi and Bo Jiang},
title = {Diastereo- and Enantioselective Construction of 3,3′-Pyrrolidinyldispirooxindole Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions},
journal = {Journal of Organic Chemistry},
year = {2015},
volume = {80},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.joc.5b00708},
number = {11},
pages = {5737--5744},
doi = {10.1021/acs.joc.5b00708}
}
Cite this
MLA
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Dai, Wei, et al. “Diastereo- and Enantioselective Construction of 3,3′-Pyrrolidinyldispirooxindole Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions.” Journal of Organic Chemistry, vol. 80, no. 11, May. 2015, pp. 5737-5744. https://doi.org/10.1021/acs.joc.5b00708.