Stereoselective Synthesis of Hydropyrano[3,2‐b]indoles via Organocatalytic Asymmetric Inverse‐Electron‐Demand Oxa‐Diels–Alder Reaction
Lei Yang
1
,
Wei Huang
1
,
Xianghong He
1
,
Ming Cheng Yang
1
,
Xiang Li
1
,
Gu He
2
,
Cheng Peng
1
,
Bo Han
1
Publication type: Journal Article
Publication date: 2016-08-03
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
General Chemistry
Abstract
Enantio- and diastereoselective inverse-electron-demand oxa-Diels–Alder reactions are described between (Z)-2-ylideneoxindoles and aldehydes in the presence of a chiral secondary amine catalyst. The corresponding hydropyrano[3,2-b]indoles are produced in up to 77% yield with up to 99% ee. Convenient synthetic transformations of the products readily lead to pharmacologically interesting scaffolds bearing multiple functional groups. This method may also provide an alternative approach for the asymmetric synthesis of 2-spirocyclo-3-oxindoles.
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Total citations:
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Citations from 2024:
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(9.76%)
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GOST
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Yang L. et al. Stereoselective Synthesis of Hydropyrano[3,2‐b]indoles via Organocatalytic Asymmetric Inverse‐Electron‐Demand Oxa‐Diels–Alder Reaction // Advanced Synthesis and Catalysis. 2016. Vol. 358. No. 18. pp. 2970-2975.
GOST all authors (up to 50)
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Yang L., Huang W., He X., Yang M. C., Li X., He G., Peng C., Han B. Stereoselective Synthesis of Hydropyrano[3,2‐b]indoles via Organocatalytic Asymmetric Inverse‐Electron‐Demand Oxa‐Diels–Alder Reaction // Advanced Synthesis and Catalysis. 2016. Vol. 358. No. 18. pp. 2970-2975.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/adsc.201600465
UR - https://doi.org/10.1002/adsc.201600465
TI - Stereoselective Synthesis of Hydropyrano[3,2‐b]indoles via Organocatalytic Asymmetric Inverse‐Electron‐Demand Oxa‐Diels–Alder Reaction
T2 - Advanced Synthesis and Catalysis
AU - Yang, Lei
AU - Huang, Wei
AU - He, Xianghong
AU - Yang, Ming Cheng
AU - Li, Xiang
AU - He, Gu
AU - Peng, Cheng
AU - Han, Bo
PY - 2016
DA - 2016/08/03
PB - Wiley
SP - 2970-2975
IS - 18
VL - 358
SN - 1615-4150
SN - 1615-4169
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2016_Yang,
author = {Lei Yang and Wei Huang and Xianghong He and Ming Cheng Yang and Xiang Li and Gu He and Cheng Peng and Bo Han},
title = {Stereoselective Synthesis of Hydropyrano[3,2‐b]indoles via Organocatalytic Asymmetric Inverse‐Electron‐Demand Oxa‐Diels–Alder Reaction},
journal = {Advanced Synthesis and Catalysis},
year = {2016},
volume = {358},
publisher = {Wiley},
month = {aug},
url = {https://doi.org/10.1002/adsc.201600465},
number = {18},
pages = {2970--2975},
doi = {10.1002/adsc.201600465}
}
Cite this
MLA
Copy
Yang, Lei, et al. “Stereoselective Synthesis of Hydropyrano[3,2‐b]indoles via Organocatalytic Asymmetric Inverse‐Electron‐Demand Oxa‐Diels–Alder Reaction.” Advanced Synthesis and Catalysis, vol. 358, no. 18, Aug. 2016, pp. 2970-2975. https://doi.org/10.1002/adsc.201600465.