volume 8 issue 12 pages 3091-3101

Oxidative α-acyloxylation of acetals with cyclic diacyl peroxides

Vera A. Vil’ 1, 2, 3, 4, 5, 6, 7
Evgenii S Gorlov 1, 3, 4, 5, 6
Bing Yu 8, 9, 10, 11, 12, 13
Alexander O. Terent'ev 1, 2, 3, 4, 5, 6, 7
Publication typeJournal Article
Publication date2021-04-12
scimago Q1
wos Q1
SJR1.068
CiteScore8.2
Impact factor4.7
ISSN20524110, 20524129
Organic Chemistry
Abstract
An acetal fragment is a well-known protective group which does not activate the neighboring α-position. Selective functionalization of the non-activated acetal α-position with formal retaining of the acetal fragment was realized using cyclic diacyl peroxides. The discovered oxidative C–O coupling of cyclic diacyl peroxides with acetals leads to α-acyloxy acetals with a free carboxylic acid group in 42–85% yields. The reaction probably proceeds via in situ enol ether formation, oxidative [5 + 2] cycloaddition, and the recovery of the acetal fragment.
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Vil’ V. A. et al. Oxidative α-acyloxylation of acetals with cyclic diacyl peroxides // Organic Chemistry Frontiers. 2021. Vol. 8. No. 12. pp. 3091-3101.
GOST all authors (up to 50) Copy
Vil’ V. A., Gorlov E. S., Yu B., Terent'ev A. O. Oxidative α-acyloxylation of acetals with cyclic diacyl peroxides // Organic Chemistry Frontiers. 2021. Vol. 8. No. 12. pp. 3091-3101.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1039/d1qo00494h
UR - https://xlink.rsc.org/?DOI=D1QO00494H
TI - Oxidative α-acyloxylation of acetals with cyclic diacyl peroxides
T2 - Organic Chemistry Frontiers
AU - Vil’, Vera A.
AU - Gorlov, Evgenii S
AU - Yu, Bing
AU - Terent'ev, Alexander O.
PY - 2021
DA - 2021/04/12
PB - Royal Society of Chemistry (RSC)
SP - 3091-3101
IS - 12
VL - 8
SN - 2052-4110
SN - 2052-4129
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Vil’,
author = {Vera A. Vil’ and Evgenii S Gorlov and Bing Yu and Alexander O. Terent'ev},
title = {Oxidative α-acyloxylation of acetals with cyclic diacyl peroxides},
journal = {Organic Chemistry Frontiers},
year = {2021},
volume = {8},
publisher = {Royal Society of Chemistry (RSC)},
month = {apr},
url = {https://xlink.rsc.org/?DOI=D1QO00494H},
number = {12},
pages = {3091--3101},
doi = {10.1039/d1qo00494h}
}
MLA
Cite this
MLA Copy
Vil’, Vera A., et al. “Oxidative α-acyloxylation of acetals with cyclic diacyl peroxides.” Organic Chemistry Frontiers, vol. 8, no. 12, Apr. 2021, pp. 3091-3101. https://xlink.rsc.org/?DOI=D1QO00494H.