Domino Reactions of Bis-Diazo Compounds: Rhodium(II) Acetate Catalyzed Diastereoselective Synthesis of Epoxy- and Epithio-Bridged Heterocycle-Fused Quinolizinone Analogues
Publication type: Journal Article
Publication date: 2016-04-13
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
Rhodium(II) acetate catalyzed domino reactions of bis-diazo compounds afford epoxy- and epithio-bridged heterocycle-fused quinolizinone systems in a stereoselective manner. The presence of an acceptor diazo functionality leads to a selective intermolecular X–H insertion reaction in a chemoselective manner, and the acceptor/acceptor diazo functionality subsequently participates in the formation of isomunchnone/thioisomunchnone 1,3-dipoles followed by intramolecular cycloaddition in a diastereoselective manner. This domino reaction is capable of constructing epoxy- and epithio-bridged heterocycle-fused quinolizinone ring systems with four stereogenic centers. The Bronsted acid induced reactions of oxa-bridged tricyclic compounds furnish ring-opened alcohol products in a regioselective manner.
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11
Total citations:
11
Citations from 2025:
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(9.09%)
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Muthusamy S., Gangadurai C. Domino Reactions of Bis-Diazo Compounds: Rhodium(II) Acetate Catalyzed Diastereoselective Synthesis of Epoxy- and Epithio-Bridged Heterocycle-Fused Quinolizinone Analogues // Synthesis. 2016. Vol. 48. No. 14. pp. 2213-2225.
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Muthusamy S., Gangadurai C. Domino Reactions of Bis-Diazo Compounds: Rhodium(II) Acetate Catalyzed Diastereoselective Synthesis of Epoxy- and Epithio-Bridged Heterocycle-Fused Quinolizinone Analogues // Synthesis. 2016. Vol. 48. No. 14. pp. 2213-2225.
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TY - JOUR
DO - 10.1055/s-0035-1560441
UR - https://doi.org/10.1055/s-0035-1560441
TI - Domino Reactions of Bis-Diazo Compounds: Rhodium(II) Acetate Catalyzed Diastereoselective Synthesis of Epoxy- and Epithio-Bridged Heterocycle-Fused Quinolizinone Analogues
T2 - Synthesis
AU - Muthusamy, S.
AU - Gangadurai, Chinnakuzhanthai
PY - 2016
DA - 2016/04/13
PB - Georg Thieme Verlag KG
SP - 2213-2225
IS - 14
VL - 48
SN - 0039-7881
SN - 1437-210X
ER -
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BibTex (up to 50 authors)
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@article{2016_Muthusamy,
author = {S. Muthusamy and Chinnakuzhanthai Gangadurai},
title = {Domino Reactions of Bis-Diazo Compounds: Rhodium(II) Acetate Catalyzed Diastereoselective Synthesis of Epoxy- and Epithio-Bridged Heterocycle-Fused Quinolizinone Analogues},
journal = {Synthesis},
year = {2016},
volume = {48},
publisher = {Georg Thieme Verlag KG},
month = {apr},
url = {https://doi.org/10.1055/s-0035-1560441},
number = {14},
pages = {2213--2225},
doi = {10.1055/s-0035-1560441}
}
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MLA
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Muthusamy, S., and Chinnakuzhanthai Gangadurai. “Domino Reactions of Bis-Diazo Compounds: Rhodium(II) Acetate Catalyzed Diastereoselective Synthesis of Epoxy- and Epithio-Bridged Heterocycle-Fused Quinolizinone Analogues.” Synthesis, vol. 48, no. 14, Apr. 2016, pp. 2213-2225. https://doi.org/10.1055/s-0035-1560441.