New Monodentate P,C-Stereogenic Bicyclic Phosphanes: 1-Phenyl-1,3a,4,5,6,6a-hexahydrocyclopenta[b]phosphole and 1-Phenyloctahydrocyclopenta[b]phosphole
Тип публикации: Journal Article
Дата публикации: 2004-09-01
SCImago Q2
WOS Q2
БС2
SJR: 0.497
CiteScore: 4.2
Impact factor: 2.8
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Краткое описание
Racemic1-phenyl-1,3a,4,5,6,6a-hexahydrocyclopenta[b]phosphole (4) was separated into enantiomerically pure 1-phenyl-1,3a,4,5,6,6a-hexahydrocyclopenta[b]phosphole 1-oxides [(RP)-6 and (SP)-6] by an oxidative resolution procedure involving treatment of 4 with menthyl bromoacetate, crystallization of the resulting diastereoisomeric phosphonium bromides 8, and stereoselective hydrolysis of the diastereomerically pure salts to the corresponding enantiomerically pure phosphane oxides. Stereoretentive reduction of P=O in (RP)-6 gave enantiomerically pure (SP)-4. Hydrogenation of (SP)-6 and subsequent reduction of P=O afforded saturated 1-phenyloctahydrocyclopenta[b]phosphole [(RP)-5]. Monophosphanes (SP)-4 and (RP)-5 were tested as chiral ligands and catalysts in model asymmetric hydrogenation and C−C bond-forming reactions. Enantioselectivities of up to 95% were observed. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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Pakulski Z. et al. New Monodentate P,C-Stereogenic Bicyclic Phosphanes: 1-Phenyl-1,3a,4,5,6,6a-hexahydrocyclopenta[b]phosphole and 1-Phenyloctahydrocyclopenta[b]phosphole // European Journal of Organic Chemistry. 2004. Vol. 2004. No. 18. pp. 3913-3918.
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Pakulski Z., Demchuk O. M., Frelek J., Luboradzki R., Pietrusiewicz K. M. New Monodentate P,C-Stereogenic Bicyclic Phosphanes: 1-Phenyl-1,3a,4,5,6,6a-hexahydrocyclopenta[b]phosphole and 1-Phenyloctahydrocyclopenta[b]phosphole // European Journal of Organic Chemistry. 2004. Vol. 2004. No. 18. pp. 3913-3918.
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TY - JOUR
DO - 10.1002/ejoc.200400186
UR - https://doi.org/10.1002/ejoc.200400186
TI - New Monodentate P,C-Stereogenic Bicyclic Phosphanes: 1-Phenyl-1,3a,4,5,6,6a-hexahydrocyclopenta[b]phosphole and 1-Phenyloctahydrocyclopenta[b]phosphole
T2 - European Journal of Organic Chemistry
AU - Pakulski, Zbigniew
AU - Demchuk, Oleg M.
AU - Frelek, Jadwiga
AU - Luboradzki, Roman
AU - Pietrusiewicz, K. Michał
PY - 2004
DA - 2004/09/01
PB - Wiley
SP - 3913-3918
IS - 18
VL - 2004
SN - 1434-193X
SN - 1099-0690
ER -
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@article{2004_Pakulski,
author = {Zbigniew Pakulski and Oleg M. Demchuk and Jadwiga Frelek and Roman Luboradzki and K. Michał Pietrusiewicz},
title = {New Monodentate P,C-Stereogenic Bicyclic Phosphanes: 1-Phenyl-1,3a,4,5,6,6a-hexahydrocyclopenta[b]phosphole and 1-Phenyloctahydrocyclopenta[b]phosphole},
journal = {European Journal of Organic Chemistry},
year = {2004},
volume = {2004},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/ejoc.200400186},
number = {18},
pages = {3913--3918},
doi = {10.1002/ejoc.200400186}
}
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MLA
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Pakulski, Zbigniew, et al. “New Monodentate P,C-Stereogenic Bicyclic Phosphanes: 1-Phenyl-1,3a,4,5,6,6a-hexahydrocyclopenta[b]phosphole and 1-Phenyloctahydrocyclopenta[b]phosphole.” European Journal of Organic Chemistry, vol. 2004, no. 18, Sep. 2004, pp. 3913-3918. https://doi.org/10.1002/ejoc.200400186.
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