том 17 издание 31 страницы 7293-7299

Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones

Тип публикацииJournal Article
Дата публикации2019-07-15
SCImago Q2
WOS Q2
БС1
SJR0.475
CiteScore4.8
Impact factor2.8
ISSN14770520, 14770539
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
The highly efficient addition of phosphorus and carbon pronucleophiles to α-methylene-γ-butyrolactones (tulipalin A and arglabin) under n-Bu3P catalysis is reported. Kinetic experiments indicate that the unprecedentedly high reactivity of α-methylene-γ-butyrolactones results from the rigid s-cis geometry of the 1-oxa-1,3-butadiene moiety that favors generation of zwitterionic intermediate stabilized by interaction between the phosphonium center and adjacent carbonyl oxygen. The presented strategy offers an economical and practical method for functionalization of natural biologically active α-methylene-γ-butyrolactones with high levels of chemo- and stereoselectivity.
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ГОСТ |
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Salin A. V. et al. Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones // Organic and Biomolecular Chemistry. 2019. Vol. 17. No. 31. pp. 7293-7299.
ГОСТ со всеми авторами (до 50) Скопировать
Salin A. V., R. Islamov D., Islamov D. R. Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones // Organic and Biomolecular Chemistry. 2019. Vol. 17. No. 31. pp. 7293-7299.
RIS |
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TY - JOUR
DO - 10.1039/c9ob01401b
UR - https://xlink.rsc.org/?DOI=C9OB01401B
TI - Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones
T2 - Organic and Biomolecular Chemistry
AU - Salin, Alexey V.
AU - R. Islamov, Daut
AU - Islamov, Daut R.
PY - 2019
DA - 2019/07/15
PB - Royal Society of Chemistry (RSC)
SP - 7293-7299
IS - 31
VL - 17
PMID - 31328762
SN - 1477-0520
SN - 1477-0539
ER -
BibTex |
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BibTex (до 50 авторов) Скопировать
@article{2019_Salin,
author = {Alexey V. Salin and Daut R. Islamov and Daut R. Islamov},
title = {Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones},
journal = {Organic and Biomolecular Chemistry},
year = {2019},
volume = {17},
publisher = {Royal Society of Chemistry (RSC)},
month = {jul},
url = {https://xlink.rsc.org/?DOI=C9OB01401B},
number = {31},
pages = {7293--7299},
doi = {10.1039/c9ob01401b}
}
MLA
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Salin, Alexey V., et al. “Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones.” Organic and Biomolecular Chemistry, vol. 17, no. 31, Jul. 2019, pp. 7293-7299. https://xlink.rsc.org/?DOI=C9OB01401B.
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