Organic Letters

, том 23 , издание 13 , страницы 5266-5270

Construction of Spiro-γ-butyrolactone Core via Cascade Photochemical Reaction of 3-Hydroxypyran-4-one Derivatives

Тип публикации: Journal Article

Дата публикации: 2021-06-21

American Chemical Society (ACS)

Organic Letters

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SJR: 1.007

CiteScore: 8.7

Impact factor: 5

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.1c01814

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PubMed ID: 34152150

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Краткое описание

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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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

PMID - 34152150

SN - 1523-7060

SN - 1523-7052

ER -

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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.

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American Chemical Society (ACS)

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Organic Letters

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