Organic Letters, volume 19, issue 14, pages 3731-3734
Styrylmalonates as an Alternative to Donor–Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones
Publication type: Journal Article
Publication date: 2017-06-29
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
A new strategy for modifying the reactivity of donor-acceptor cyclopropanes (DAC) has been suggested. It involves the use of isomeric styrylmalonates as alternative sources of reactive intermediates. The efficiency of the approach has been demonstrated in reactions with aromatic aldehydes. As a result, a new process for construction of the 5,6-dihydropyran-2-one skeleton has been developed. It efficiently occurs with high diastereoselectivity in the presence of BF3·Et2O; the products can be easily isolated by crystallization. The subsequent use of the resulting dihydropyranones in syntheses providing convenient access to various classes of compounds with broad molecular diversity has been demonstrated.
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GOST
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Borisov D. D. et al. Styrylmalonates as an Alternative to Donor–Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones // Organic Letters. 2017. Vol. 19. No. 14. pp. 3731-3734.
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Borisov D. D., Novikov R. G., Eltysheva A. S., Tkachev Y. V., Tomilov Y. V. Styrylmalonates as an Alternative to Donor–Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones // Organic Letters. 2017. Vol. 19. No. 14. pp. 3731-3734.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.7b01556
UR - https://doi.org/10.1021/acs.orglett.7b01556
TI - Styrylmalonates as an Alternative to Donor–Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones
T2 - Organic Letters
AU - Borisov, Denis D
AU - Novikov, Roman G.
AU - Eltysheva, Anna S
AU - Tkachev, Yaroslav V.
AU - Tomilov, Yury V.
PY - 2017
DA - 2017/06/29
PB - American Chemical Society (ACS)
SP - 3731-3734
IS - 14
VL - 19
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2017_Borisov,
author = {Denis D Borisov and Roman G. Novikov and Anna S Eltysheva and Yaroslav V. Tkachev and Yury V. Tomilov},
title = {Styrylmalonates as an Alternative to Donor–Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones},
journal = {Organic Letters},
year = {2017},
volume = {19},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.orglett.7b01556},
number = {14},
pages = {3731--3734},
doi = {10.1021/acs.orglett.7b01556}
}
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Borisov, Denis D., et al. “Styrylmalonates as an Alternative to Donor–Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones.” Organic Letters, vol. 19, no. 14, Jun. 2017, pp. 3731-3734. https://doi.org/10.1021/acs.orglett.7b01556.
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