Silylcyclopropanes by Selective [1,4]-Wittig Rearrangement of 4-Silyl-5,6-dihydropyrans
Publication type: Journal Article
Publication date: 2021-07-08
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
34236869
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
4-Silyl-5,6-dihydropyrans undergo remarkably selective [1,4]-Wittig rearrangements to give silylcyclopropanes in good yields. The selectivity is independent of the silyl group, but it is influenced by the electronic character of the migrating center. Electron-rich and electron-neutral (hetero)aryl groups and aliphatic substituents at the migrating center lead to exclusive [1,4]-migration, whereas electron-deficient aryl groups predominantly afford [1,2]-Wittig products.
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Mori Quiroz L. M., Maloba E. W., Maleczka R. E. Silylcyclopropanes by Selective [1,4]-Wittig Rearrangement of 4-Silyl-5,6-dihydropyrans // Organic Letters. 2021. Vol. 23. No. 15. pp. 5724-5728.
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Mori Quiroz L. M., Maloba E. W., Maleczka R. E. Silylcyclopropanes by Selective [1,4]-Wittig Rearrangement of 4-Silyl-5,6-dihydropyrans // Organic Letters. 2021. Vol. 23. No. 15. pp. 5724-5728.
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TY - JOUR
DO - 10.1021/acs.orglett.1c01838
UR - https://doi.org/10.1021/acs.orglett.1c01838
TI - Silylcyclopropanes by Selective [1,4]-Wittig Rearrangement of 4-Silyl-5,6-dihydropyrans
T2 - Organic Letters
AU - Mori Quiroz, Luis M
AU - Maloba, Emmanuel W
AU - Maleczka, Robert E.
PY - 2021
DA - 2021/07/08
PB - American Chemical Society (ACS)
SP - 5724-5728
IS - 15
VL - 23
PMID - 34236869
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2021_Mori Quiroz,
author = {Luis M Mori Quiroz and Emmanuel W Maloba and Robert E. Maleczka},
title = {Silylcyclopropanes by Selective [1,4]-Wittig Rearrangement of 4-Silyl-5,6-dihydropyrans},
journal = {Organic Letters},
year = {2021},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.orglett.1c01838},
number = {15},
pages = {5724--5728},
doi = {10.1021/acs.orglett.1c01838}
}
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MLA
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Mori Quiroz, Luis M., et al. “Silylcyclopropanes by Selective [1,4]-Wittig Rearrangement of 4-Silyl-5,6-dihydropyrans.” Organic Letters, vol. 23, no. 15, Jul. 2021, pp. 5724-5728. https://doi.org/10.1021/acs.orglett.1c01838.