Walphos versus Biferrocene-Based Walphos Analogues in the Asymmetric Hydrogenation of Alkenes and Ketones
Afrooz Zirakzadeh
1, 2
,
Manuela A Gross
1, 3
,
Yaping Wang
4
,
K. Mereiter
5
,
Walter Weissensteiner
1
1
Тип публикации: Journal Article
Дата публикации: 2014-04-09
scimago Q2
wos Q1
БС1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
PubMed ID:
24795493
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Краткое описание
Two representative Walphos analogues with an achiral 2,2″-biferrocenediyl backbone were synthesized. These diphosphine ligands were tested in the rhodium-catalyzed asymmetric hydrogenation of several alkenes and in the ruthenium-catalyzed hydrogenation of two ketones. The results were compared with those previously obtained on using biferrocene ligands with a C2-symmetric 2,2″-biferrocenediyl backbone as well as with those obtained with Walphos ligands. The application of one newly synthesized ligand in the hydrogenation of 2-methylcinnamic acid gave (R)-2-methyl-3-phenylpropanoic acid with full conversion and with 92% ee. The same ligand was used to transform 2,4-pentanedione quantitatively and diastereoselectively into (S,S)-2,4-pentanediol with 98% ee.
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Zirakzadeh A. et al. Walphos versus Biferrocene-Based Walphos Analogues in the Asymmetric Hydrogenation of Alkenes and Ketones // Organometallics. 2014. Vol. 33. No. 8. pp. 1945-1952.
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Zirakzadeh A., Gross M. A., Wang Y., Mereiter K., Weissensteiner W. Walphos versus Biferrocene-Based Walphos Analogues in the Asymmetric Hydrogenation of Alkenes and Ketones // Organometallics. 2014. Vol. 33. No. 8. pp. 1945-1952.
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TY - JOUR
DO - 10.1021/om401074a
UR - https://doi.org/10.1021/om401074a
TI - Walphos versus Biferrocene-Based Walphos Analogues in the Asymmetric Hydrogenation of Alkenes and Ketones
T2 - Organometallics
AU - Zirakzadeh, Afrooz
AU - Gross, Manuela A
AU - Wang, Yaping
AU - Mereiter, K.
AU - Weissensteiner, Walter
PY - 2014
DA - 2014/04/09
PB - American Chemical Society (ACS)
SP - 1945-1952
IS - 8
VL - 33
PMID - 24795493
SN - 0276-7333
SN - 1520-6041
ER -
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@article{2014_Zirakzadeh,
author = {Afrooz Zirakzadeh and Manuela A Gross and Yaping Wang and K. Mereiter and Walter Weissensteiner},
title = {Walphos versus Biferrocene-Based Walphos Analogues in the Asymmetric Hydrogenation of Alkenes and Ketones},
journal = {Organometallics},
year = {2014},
volume = {33},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/om401074a},
number = {8},
pages = {1945--1952},
doi = {10.1021/om401074a}
}
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MLA
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Zirakzadeh, Afrooz, et al. “Walphos versus Biferrocene-Based Walphos Analogues in the Asymmetric Hydrogenation of Alkenes and Ketones.” Organometallics, vol. 33, no. 8, Apr. 2014, pp. 1945-1952. https://doi.org/10.1021/om401074a.