Organic Letters, volume 23, issue 13, pages 5266-5270
Construction of Spiro-γ-butyrolactone Core via Cascade Photochemical Reaction of 3-Hydroxypyran-4-one Derivatives
1
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, Moscow 119991, Russian Federation
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Publication type: Journal Article
Publication date: 2021-06-21
Journal:
Organic Letters
Q1
Q1
SJR: 1.245
CiteScore: 9.3
Impact factor: 4.9
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
We elaborate a novel one-step photochemical method for the synthesis of spiro-γ-butyrolactone derivatives from 3-hydroxypyran-4-ones. The suggested approach is based on a cascade process including initial photoinduced contraction of 4-pyranone ring followed by intramolecular cyclization leading to the final spiro system. A distinctive feature of the proposed method is intramolecular trapping of unstable α-hydroxydiketone intermediate formed in situ as a result of a photochemical reaction. The structures of two synthesized 1-oxaspiro[4.4]non-8-ene-2,6,7-triones were determined by X-ray diffraction.
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Milyutin C. V. et al. Construction of Spiro-γ-butyrolactone Core via Cascade Photochemical Reaction of 3-Hydroxypyran-4-one Derivatives // Organic Letters. 2021. Vol. 23. No. 13. pp. 5266-5270.
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Milyutin C. V., Komogortsev A., Lichitsky B., Lichitsky B. V., Melekhina V. G., Minyaev M. E. Construction of Spiro-γ-butyrolactone Core via Cascade Photochemical Reaction of 3-Hydroxypyran-4-one Derivatives // Organic Letters. 2021. Vol. 23. No. 13. pp. 5266-5270.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.1c01814
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.1c01814
TI - Construction of Spiro-γ-butyrolactone Core via Cascade Photochemical Reaction of 3-Hydroxypyran-4-one Derivatives
T2 - Organic Letters
AU - Milyutin, Constantine V
AU - Komogortsev, Andrey
AU - Lichitsky, Boris
AU - Lichitsky, Boris V
AU - Melekhina, Valeriya G
AU - Minyaev, Mikhail E.
PY - 2021
DA - 2021/06/21
PB - American Chemical Society (ACS)
SP - 5266-5270
IS - 13
VL - 23
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2021_Milyutin,
author = {Constantine V Milyutin and Andrey Komogortsev and Boris Lichitsky and Boris V Lichitsky and Valeriya G Melekhina and Mikhail E. Minyaev},
title = {Construction of Spiro-γ-butyrolactone Core via Cascade Photochemical Reaction of 3-Hydroxypyran-4-one Derivatives},
journal = {Organic Letters},
year = {2021},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.1c01814},
number = {13},
pages = {5266--5270},
doi = {10.1021/acs.orglett.1c01814}
}
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Milyutin, Constantine V., et al. “Construction of Spiro-γ-butyrolactone Core via Cascade Photochemical Reaction of 3-Hydroxypyran-4-one Derivatives.” Organic Letters, vol. 23, no. 13, Jun. 2021, pp. 5266-5270. https://pubs.acs.org/doi/10.1021/acs.orglett.1c01814.