Catalytic cyclopropanation of spiro[2.4]hepta-4,6-diene with diazomethane
Publication type: Journal Article
Publication date: 2019-08-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
• Catalytic cyclopropanation of spiro[2.4]hepta-4,6-diene with diazomethane was studied. • The process is catalyzed by compounds of copper, iron and palladium. • The catalyst allows to control the regio- and stereoselectivity of the reaction. • Both mono- and dicyclopropanation products are obtained. • Safe and efficient procedure with diazomethane generated in situ was used. Catalytic cyclopropanation of spiro[2.4]hepta-4,6-diene with diazomethane in the presence of copper or palladium compounds results in mono- and dicyclopropanation products, namely, spiro[bicyclo[3.1.0]hex-3-ene-2,1′-cyclopropane] and spiro[cyclopropane-1,5′-tricyclo[4.1.0.0 2,4 ]heptane], with different efficiency. The use of Pd compounds as catalysts allows the cyclopropanation to be performed under conditions of simultaneous generation and decomposition of diazomethane.
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Shulishov E. V. et al. Catalytic cyclopropanation of spiro[2.4]hepta-4,6-diene with diazomethane // Tetrahedron Letters. 2019. Vol. 60. No. 31. pp. 2043-2045.
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Shulishov E. V., Pantyukh O. A., Menchikov L. G., Tomilov Y. V. Catalytic cyclopropanation of spiro[2.4]hepta-4,6-diene with diazomethane // Tetrahedron Letters. 2019. Vol. 60. No. 31. pp. 2043-2045.
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TY - JOUR
DO - 10.1016/j.tetlet.2019.06.044
UR - https://doi.org/10.1016/j.tetlet.2019.06.044
TI - Catalytic cyclopropanation of spiro[2.4]hepta-4,6-diene with diazomethane
T2 - Tetrahedron Letters
AU - Shulishov, Evgeny V.
AU - Pantyukh, Olga A
AU - Menchikov, Leonid G
AU - Tomilov, Yury V.
PY - 2019
DA - 2019/08/01
PB - Elsevier
SP - 2043-2045
IS - 31
VL - 60
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2019_Shulishov,
author = {Evgeny V. Shulishov and Olga A Pantyukh and Leonid G Menchikov and Yury V. Tomilov},
title = {Catalytic cyclopropanation of spiro[2.4]hepta-4,6-diene with diazomethane},
journal = {Tetrahedron Letters},
year = {2019},
volume = {60},
publisher = {Elsevier},
month = {aug},
url = {https://doi.org/10.1016/j.tetlet.2019.06.044},
number = {31},
pages = {2043--2045},
doi = {10.1016/j.tetlet.2019.06.044}
}
Cite this
MLA
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Shulishov, Evgeny V., et al. “Catalytic cyclopropanation of spiro[2.4]hepta-4,6-diene with diazomethane.” Tetrahedron Letters, vol. 60, no. 31, Aug. 2019, pp. 2043-2045. https://doi.org/10.1016/j.tetlet.2019.06.044.