Rhodium-catalyzed asymmetric hydrogenations of electron deficient olefins using 1,4-diphosphine ligands bearing an imidazolidin-2-one backbone

Sang gi Lee; Yong Jian Zhang

doi:10.1016/S0957-4166(02)00243-4

Rhodium-catalyzed asymmetric hydrogenations of electron deficient olefins using 1,4-diphosphine ligands bearing an imidazolidin-2-one backbone

Sang gi Lee, Yong Jian Zhang

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

In rhodium(I)-catalyzed asymmetric hydrogenations of electron deficient olefins, the electron-rich and sterically encumbered phosphine ligand, MOD-BDPMI, exhibited higher enantioselectivities than BDPMI ligands. Moreover, the N-substituents of the imidazolidin-2-one backbone affected the enantioselectivity. Thus, using the N,N′-dimethylated MOD-BDPMI ligand 2b, (Z)-α-(N-acetamido)cinnamic acid 3 was hydrogenated with 100% conversion to give the saturated α-amino acid with ee of 88.7%.

Original language	English
Pages (from-to)	1039-1042
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	13
Issue number	10
DOIs	https://doi.org/10.1016/S0957-4166(02)00243-4
State	Published - 10 Jun 2002

Bibliographical note

Funding Information:
We are grateful for financial support from the Ministry of Science and Technology (National Research Laboratory Program, 2N22890), from KIST (2E17512) and CMDS at KAIST.

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10.1016/S0957-4166(02)00243-4

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title = "Rhodium-catalyzed asymmetric hydrogenations of electron deficient olefins using 1,4-diphosphine ligands bearing an imidazolidin-2-one backbone",

abstract = "In rhodium(I)-catalyzed asymmetric hydrogenations of electron deficient olefins, the electron-rich and sterically encumbered phosphine ligand, MOD-BDPMI, exhibited higher enantioselectivities than BDPMI ligands. Moreover, the N-substituents of the imidazolidin-2-one backbone affected the enantioselectivity. Thus, using the N,N′-dimethylated MOD-BDPMI ligand 2b, (Z)-α-(N-acetamido)cinnamic acid 3 was hydrogenated with 100% conversion to give the saturated α-amino acid with ee of 88.7%.",

author = "Lee, {Sang gi} and Zhang, {Yong Jian}",

note = "Funding Information: We are grateful for financial support from the Ministry of Science and Technology (National Research Laboratory Program, 2N22890), from KIST (2E17512) and CMDS at KAIST.",

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T1 - Rhodium-catalyzed asymmetric hydrogenations of electron deficient olefins using 1,4-diphosphine ligands bearing an imidazolidin-2-one backbone

AU - Lee, Sang gi

AU - Zhang, Yong Jian

N1 - Funding Information: We are grateful for financial support from the Ministry of Science and Technology (National Research Laboratory Program, 2N22890), from KIST (2E17512) and CMDS at KAIST.

PY - 2002/6/10

Y1 - 2002/6/10

N2 - In rhodium(I)-catalyzed asymmetric hydrogenations of electron deficient olefins, the electron-rich and sterically encumbered phosphine ligand, MOD-BDPMI, exhibited higher enantioselectivities than BDPMI ligands. Moreover, the N-substituents of the imidazolidin-2-one backbone affected the enantioselectivity. Thus, using the N,N′-dimethylated MOD-BDPMI ligand 2b, (Z)-α-(N-acetamido)cinnamic acid 3 was hydrogenated with 100% conversion to give the saturated α-amino acid with ee of 88.7%.

AB - In rhodium(I)-catalyzed asymmetric hydrogenations of electron deficient olefins, the electron-rich and sterically encumbered phosphine ligand, MOD-BDPMI, exhibited higher enantioselectivities than BDPMI ligands. Moreover, the N-substituents of the imidazolidin-2-one backbone affected the enantioselectivity. Thus, using the N,N′-dimethylated MOD-BDPMI ligand 2b, (Z)-α-(N-acetamido)cinnamic acid 3 was hydrogenated with 100% conversion to give the saturated α-amino acid with ee of 88.7%.

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Rhodium-catalyzed asymmetric hydrogenations of electron deficient olefins using 1,4-diphosphine ligands bearing an imidazolidin-2-one backbone

Abstract

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