Chiral Squaramide-Catalyzed Michael/Alkylation Cascade Reaction for the Asymmetric Synthesis of Nitro-Spirocyclopropanes
Publication type: Journal Article
Publication date: 2015-07-22
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A new diastereoselective and enantioselective cyclopropanation reaction has been developed by employing a Michael/alkylation cascade reaction between (E)-3-arylenechroman-4-one or (E)-2-arylideneindan-1-one derivatives and a bromonitroalkane with a chiral squaramide catalyst. This reaction constitutes a facile asymmetric synthesis for nitro-spirocyclopropanes that have three adjacent stereogenic centers, including one quaternary center, in moderate to good yields (up to 90 %) with excellent enantio- [up to >99 % ee (enantiomeric excess)] and diastereoselectivities [up to >99:1 dr (diastereomeric ratio)].
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41
Total citations:
41
Citations from 2025:
2
(4.88%)
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GOST
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Zhao B. L., Du D. Chiral Squaramide-Catalyzed Michael/Alkylation Cascade Reaction for the Asymmetric Synthesis of Nitro-Spirocyclopropanes // European Journal of Organic Chemistry. 2015. Vol. 2015. No. 24. pp. 5350-5359.
GOST all authors (up to 50)
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Zhao B. L., Du D. Chiral Squaramide-Catalyzed Michael/Alkylation Cascade Reaction for the Asymmetric Synthesis of Nitro-Spirocyclopropanes // European Journal of Organic Chemistry. 2015. Vol. 2015. No. 24. pp. 5350-5359.
Cite this
RIS
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TY - JOUR
DO - 10.1002/ejoc.201500533
UR - https://doi.org/10.1002/ejoc.201500533
TI - Chiral Squaramide-Catalyzed Michael/Alkylation Cascade Reaction for the Asymmetric Synthesis of Nitro-Spirocyclopropanes
T2 - European Journal of Organic Chemistry
AU - Zhao, Bo Liang
AU - Du, Daming
PY - 2015
DA - 2015/07/22
PB - Wiley
SP - 5350-5359
IS - 24
VL - 2015
SN - 1434-193X
SN - 1099-0690
ER -
Cite this
BibTex (up to 50 authors)
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@article{2015_Zhao,
author = {Bo Liang Zhao and Daming Du},
title = {Chiral Squaramide-Catalyzed Michael/Alkylation Cascade Reaction for the Asymmetric Synthesis of Nitro-Spirocyclopropanes},
journal = {European Journal of Organic Chemistry},
year = {2015},
volume = {2015},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/ejoc.201500533},
number = {24},
pages = {5350--5359},
doi = {10.1002/ejoc.201500533}
}
Cite this
MLA
Copy
Zhao, Bo Liang, and Daming Du. “Chiral Squaramide-Catalyzed Michael/Alkylation Cascade Reaction for the Asymmetric Synthesis of Nitro-Spirocyclopropanes.” European Journal of Organic Chemistry, vol. 2015, no. 24, Jul. 2015, pp. 5350-5359. https://doi.org/10.1002/ejoc.201500533.