Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones
Sofia O Samultceva
1, 2
,
Marina Yu. Dvorko
1, 2
,
Dmitrii A. Shabalin
1, 2
,
Igor A. Ushakov
1, 2
,
Alexander V. Vashchenko
1, 2
,
Elena Yu. Schmidt
1, 2
,
B. A. Trofimov
1, 2
Publication type: Journal Article
Publication date: 2022-06-15
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
35735091
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
6-Methylene-5-oxaspiro[2.4]heptanones have been synthesized via base-catalyzed dimerization of available alkynyl cyclopropyl ketones. The reaction proceeds effectively in the presence of the t-BuOK/t-BuOH/THF catalytic system at room temperature to afford the desired spirocycles in a regio- and stereoselective manner. A wider synthetic utility of alkynyl cyclopropyl ketones as novel building blocks was demonstrated by the synthesis of diverse spirocyclopropanes.
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Total citations:
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Samultceva S. O. et al. Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones // Organic and Biomolecular Chemistry. 2022. Vol. 20. No. 26. pp. 5325-5333.
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Samultceva S. O., Dvorko M. Y., Shabalin D. A., Ushakov I. A., Vashchenko A. V., Schmidt E. Y., Trofimov B. A. Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones // Organic and Biomolecular Chemistry. 2022. Vol. 20. No. 26. pp. 5325-5333.
Cite this
RIS
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TY - JOUR
DO - 10.1039/d2ob00854h
UR - https://xlink.rsc.org/?DOI=D2OB00854H
TI - Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones
T2 - Organic and Biomolecular Chemistry
AU - Samultceva, Sofia O
AU - Dvorko, Marina Yu.
AU - Shabalin, Dmitrii A.
AU - Ushakov, Igor A.
AU - Vashchenko, Alexander V.
AU - Schmidt, Elena Yu.
AU - Trofimov, B. A.
PY - 2022
DA - 2022/06/15
PB - Royal Society of Chemistry (RSC)
SP - 5325-5333
IS - 26
VL - 20
PMID - 35735091
SN - 1477-0520
SN - 1477-0539
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2022_Samultceva,
author = {Sofia O Samultceva and Marina Yu. Dvorko and Dmitrii A. Shabalin and Igor A. Ushakov and Alexander V. Vashchenko and Elena Yu. Schmidt and B. A. Trofimov},
title = {Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones},
journal = {Organic and Biomolecular Chemistry},
year = {2022},
volume = {20},
publisher = {Royal Society of Chemistry (RSC)},
month = {jun},
url = {https://xlink.rsc.org/?DOI=D2OB00854H},
number = {26},
pages = {5325--5333},
doi = {10.1039/d2ob00854h}
}
Cite this
MLA
Copy
Samultceva, Sofia O., et al. “Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones.” Organic and Biomolecular Chemistry, vol. 20, no. 26, Jun. 2022, pp. 5325-5333. https://xlink.rsc.org/?DOI=D2OB00854H.
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