Highly efficient desymmetrization of cyclopropenes to azabicyclo[3.1.0]hexanes with five continuous stereogenic centers by copper-catalyzed [3 + 2] cycloadditions
Yang Yuan
1
,
Zhanjiang Zheng
1
,
Fei Ye
1
,
Jun Han Ma
1
,
Jun-Han Ma
1
,
Xing Feng Bai
1
,
Xing-Feng Bai
1
,
Li Li
1
,
Liwen Xu
1, 2
Publication type: Journal Article
Publication date: 2018-08-01
scimago Q1
wos Q1
SJR: 1.068
CiteScore: 8.2
Impact factor: 4.7
ISSN: 20524110, 20524129
Organic Chemistry
Abstract
An unprecedented copper-catalyzed desymmetrization/cycloaddition of 1,1-disubstituted cyclopropenes to azabicyclo[3.1.0]hexane-based heterocycles containing cyclopropane and pyrrolidine motif has been developed. The salient features of the one-time simultaneous construction of five continuous carbon-stereogenic centers for the straightforward and atom-economical synthesis of chiral azabicyclo[3.1.0]hexane derivatives include a general and broad substrate scope with high yields as well as excellent diastereoselectivities (>99 : 1 dr) and excellent enantioselectivities (up to >99% ee). In addition, it is probable that the weak coordination of an amide moiety on 1,1-disubstituted cyclopropenes with the copper complex is the main reason for the tuning of the stereoselectivity of the cycloaddition reaction.
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Total citations:
26
Citations from 2024:
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(23.07%)
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GOST
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Yuan Y. et al. Highly efficient desymmetrization of cyclopropenes to azabicyclo[3.1.0]hexanes with five continuous stereogenic centers by copper-catalyzed [3 + 2] cycloadditions // Organic Chemistry Frontiers. 2018. Vol. 5. No. 18. pp. 2759-2764.
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Yuan Y., Zheng Z., Ye F., Ma J. H., Ma J., Bai X. F., Bai X., Li L., Xu L. Highly efficient desymmetrization of cyclopropenes to azabicyclo[3.1.0]hexanes with five continuous stereogenic centers by copper-catalyzed [3 + 2] cycloadditions // Organic Chemistry Frontiers. 2018. Vol. 5. No. 18. pp. 2759-2764.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/C8QO00761F
UR - https://doi.org/10.1039/C8QO00761F
TI - Highly efficient desymmetrization of cyclopropenes to azabicyclo[3.1.0]hexanes with five continuous stereogenic centers by copper-catalyzed [3 + 2] cycloadditions
T2 - Organic Chemistry Frontiers
AU - Yuan, Yang
AU - Zheng, Zhanjiang
AU - Ye, Fei
AU - Ma, Jun Han
AU - Ma, Jun-Han
AU - Bai, Xing Feng
AU - Bai, Xing-Feng
AU - Li, Li
AU - Xu, Liwen
PY - 2018
DA - 2018/08/01
PB - Royal Society of Chemistry (RSC)
SP - 2759-2764
IS - 18
VL - 5
SN - 2052-4110
SN - 2052-4129
ER -
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BibTex (up to 50 authors)
Copy
@article{2018_Yuan,
author = {Yang Yuan and Zhanjiang Zheng and Fei Ye and Jun Han Ma and Jun-Han Ma and Xing Feng Bai and Xing-Feng Bai and Li Li and Liwen Xu},
title = {Highly efficient desymmetrization of cyclopropenes to azabicyclo[3.1.0]hexanes with five continuous stereogenic centers by copper-catalyzed [3 + 2] cycloadditions},
journal = {Organic Chemistry Frontiers},
year = {2018},
volume = {5},
publisher = {Royal Society of Chemistry (RSC)},
month = {aug},
url = {https://doi.org/10.1039/C8QO00761F},
number = {18},
pages = {2759--2764},
doi = {10.1039/C8QO00761F}
}
Cite this
MLA
Copy
Yuan, Yang, et al. “Highly efficient desymmetrization of cyclopropenes to azabicyclo[3.1.0]hexanes with five continuous stereogenic centers by copper-catalyzed [3 + 2] cycloadditions.” Organic Chemistry Frontiers, vol. 5, no. 18, Aug. 2018, pp. 2759-2764. https://doi.org/10.1039/C8QO00761F.