Asymmetric [3 + 2] Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and α,β-Enones with Divergent Diastereocontrol on the Spiro[pyrrolidine-oxindoles]
Publication type: Journal Article
Publication date: 2017-03-28
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
28349684
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A general and practical organocatalytic asymmetric 1,3-dipolar cycloaddition of 3-amino oxindole-based azomethine ylides and α,β-enones has been developed. This reaction delivered spiro[pyrrolidine-2,3'-oxindole] products in high yields with excellent regio- and enantioselectivities (up to 99% yield, >20:1 rr, 99% ee). In addition, an array of spiro[dihydropyrrole-2,3'-oxindoles] were readily accessed by oxidative dehydrogenation. Notably, the inversion of the diastereoselectivity of the spiro[pyrrolidine-oxindole] product could be easily achieved through a facile oxidation-reduction process.
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73
Total citations:
73
Citations from 2024:
10
(13.7%)
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GOST
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Zhu G. et al. Asymmetric [3 + 2] Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and α,β-Enones with Divergent Diastereocontrol on the Spiro[pyrrolidine-oxindoles] // Organic Letters. 2017. Vol. 19. No. 7. pp. 1862-1865.
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Zhu G., Qian W., CHEN H., Zhang Y., Shen W., Qu J., Wang B. Asymmetric [3 + 2] Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and α,β-Enones with Divergent Diastereocontrol on the Spiro[pyrrolidine-oxindoles] // Organic Letters. 2017. Vol. 19. No. 7. pp. 1862-1865.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.7b00625
UR - https://doi.org/10.1021/acs.orglett.7b00625
TI - Asymmetric [3 + 2] Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and α,β-Enones with Divergent Diastereocontrol on the Spiro[pyrrolidine-oxindoles]
T2 - Organic Letters
AU - Zhu, Guodong
AU - Qian, Wei
AU - CHEN, Hongbo
AU - Zhang, Yanpeng
AU - Shen, Wen
AU - Qu, Jingping
AU - Wang, Baomin
PY - 2017
DA - 2017/03/28
PB - American Chemical Society (ACS)
SP - 1862-1865
IS - 7
VL - 19
PMID - 28349684
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2017_Zhu,
author = {Guodong Zhu and Wei Qian and Hongbo CHEN and Yanpeng Zhang and Wen Shen and Jingping Qu and Baomin Wang},
title = {Asymmetric [3 + 2] Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and α,β-Enones with Divergent Diastereocontrol on the Spiro[pyrrolidine-oxindoles]},
journal = {Organic Letters},
year = {2017},
volume = {19},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.orglett.7b00625},
number = {7},
pages = {1862--1865},
doi = {10.1021/acs.orglett.7b00625}
}
Cite this
MLA
Copy
Zhu, Guodong, et al. “Asymmetric [3 + 2] Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and α,β-Enones with Divergent Diastereocontrol on the Spiro[pyrrolidine-oxindoles].” Organic Letters, vol. 19, no. 7, Mar. 2017, pp. 1862-1865. https://doi.org/10.1021/acs.orglett.7b00625.
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