Diastereoselective [4+2] Cycloaddition Reaction of 1-Neomenthyl-1,2-diphosphole: Facile Synthesis ofP-Chiral Cage Phosphines
Publication type: Journal Article
Publication date: 2015-07-23
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
3,4,5-Triphenyl-1-(+)-neomenthyl-1,2-diphosphole was obtained by alkylation of sodium 3,4,5-triphenyl-1,2-diphosphacyclopentadienide with (–)-menthyl tosylate. High delocalization within the planar heterocycle of the diphosphole is indicative of low aromaticity. Thus, the [4+2] cycloaddition reaction of this compound with maleic anhydride proceeded under mild conditions with high diastereoselectivity (up to 88 % de) and resulted in the corresponding enantiopure 1,7-diphosphanorbornadiene as an individual enantiomer. The observed high diastereoselectivity may be explained by thermodynamic control of the reaction.
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Total citations:
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Citations from 2024:
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GOST
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Zagidullin A. A. et al. Diastereoselective [4+2] Cycloaddition Reaction of 1-Neomenthyl-1,2-diphosphole: Facile Synthesis ofP-Chiral Cage Phosphines // European Journal of Organic Chemistry. 2015. Vol. 2015. No. 24. pp. 5326-5329.
GOST all authors (up to 50)
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Zagidullin A. A., Miluykov V., Polyancev F. M., Latypov S., Sinyashin O. G., Lönnecke P., Hey-Hawkins E. Diastereoselective [4+2] Cycloaddition Reaction of 1-Neomenthyl-1,2-diphosphole: Facile Synthesis ofP-Chiral Cage Phosphines // European Journal of Organic Chemistry. 2015. Vol. 2015. No. 24. pp. 5326-5329.
Cite this
RIS
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TY - JOUR
DO - 10.1002/ejoc.201500558
UR - https://doi.org/10.1002/ejoc.201500558
TI - Diastereoselective [4+2] Cycloaddition Reaction of 1-Neomenthyl-1,2-diphosphole: Facile Synthesis ofP-Chiral Cage Phosphines
T2 - European Journal of Organic Chemistry
AU - Zagidullin, Almaz A
AU - Miluykov, Vasili
AU - Polyancev, Fedor M
AU - Latypov, Shamil
AU - Sinyashin, Oleg G.
AU - Lönnecke, Peter
AU - Hey-Hawkins, Evamarie
PY - 2015
DA - 2015/07/23
PB - Wiley
SP - 5326-5329
IS - 24
VL - 2015
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2015_Zagidullin,
author = {Almaz A Zagidullin and Vasili Miluykov and Fedor M Polyancev and Shamil Latypov and Oleg G. Sinyashin and Peter Lönnecke and Evamarie Hey-Hawkins},
title = {Diastereoselective [4+2] Cycloaddition Reaction of 1-Neomenthyl-1,2-diphosphole: Facile Synthesis ofP-Chiral Cage Phosphines},
journal = {European Journal of Organic Chemistry},
year = {2015},
volume = {2015},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/ejoc.201500558},
number = {24},
pages = {5326--5329},
doi = {10.1002/ejoc.201500558}
}
Cite this
MLA
Copy
Zagidullin, Almaz A., et al. “Diastereoselective [4+2] Cycloaddition Reaction of 1-Neomenthyl-1,2-diphosphole: Facile Synthesis ofP-Chiral Cage Phosphines.” European Journal of Organic Chemistry, vol. 2015, no. 24, Jul. 2015, pp. 5326-5329. https://doi.org/10.1002/ejoc.201500558.
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