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Synthesis of Diastereomeric 1,4-Diphosphine Ligands Bearing Imidazolidin-2-one Backbone and Their Application in Rh(I)-Catalyzed Asymmetric Hydrogenation of Functionalized Olefins

Title
Synthesis of Diastereomeric 1,4-Diphosphine Ligands Bearing Imidazolidin-2-one Backbone and Their Application in Rh(I)-Catalyzed Asymmetric Hydrogenation of Functionalized Olefins
Author
나명수
Keywords
asymmetric hydrogenation; backbone chirality; diphosphine ligands; olefins; rhodium
Issue Date
2005-03
Publisher
WILEY-V C H VERLAG GMBH
Citation
ADVANCED SYNTHESIS & CATALYSIS, v. 347, No. 4, Page. 563-570
Abstract
The diastereomeric 1,4-diphosphine ligands, (S,S,S,S)-1a, (R,S,S,R)-1b and (R,S,S,S)-1c, with the imidazolidin-2-one backbone were synthesized, and utilized for an investigation of the effects of backbone chirality on the enantioselectivity in the Rh(I)-catalyzed hydrogenation of various functionalized olefinic substrates. It was found that the catalytic efficiencies are largely dependent on the configurations of the alpha-carbons to phosphine. Thus, the Rh complex of the pseudo-C-2-symmetrical diphosphine, (R,S,S,S)-1c, showed excellent enantioselectivities (93.0-98.6% ees) in the hydrogenations of a broad spectrum of substrates, and especially in the hydrogenations of methyl alpha-(N-acetyamino)-beta-arylacrylates (95.3-97.0% ees). However, the enantioselectivities obtained with the C-2-symmetrical (R,S,S,R)-1b were largely dependent on the substrate (19.8-97.3% ees). The Rh complex of ligand la having the (S,S,S,S)-configuration showed the lowest catalytic efficiency for all of the substrates examined (0-84.8% ees).
URI
https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.200404286http://repository.hanyang.ac.kr/handle/20.500.11754/110246
ISSN
1615-4150; 1615-4169
DOI
10.1002/adsc.200404286
Appears in Collections:
COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY[E](과학기술융합대학) > ETC
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